Accidentally Best Friends
by witandwaldorf
Summary: 4 years ago, calling Blair Waldorf a best friend, let alone a friend, would have been unfathomable to Dan Humphrey. But 3 years later, Blair is indeed his best friend and their friendship is easy and comfortable. Until it's called into question and it's suggested they might be more than just friends. The foundation begins to crack as they explore the idea of a romantic connection.
1. Chapter 1

As Dan Humphrey rounded the corner of the bustling 6th Avenue he could already hear the sound of her heels clicking, impatiently. Of course, he wasn't within earshot of her, but knowing Blair Waldorf, four minutes late was enough to cause her to be jittering with annoyance. Spotting her just ahead, Dan was gratified to see he was right. There she was, her magenta suede Manolos tapping the ground anxiously. Spotting him, she narrowed her eyes and slouched in annoyance.

"There you are Humphrey, is it so hard to be on time? It's not like you take the time to make yourself presentable," She wrinkles her nose as she visibly scrutinizes his hair and then outfit. "So tell me what it is that caused you to be so late?"

"Hello to you too Blair," Dan says, handing her a ticket. "It's only four minutes after the hour."

"Five, actually." She says after scanning the face of her Cartier watch. "Let's go inside. You know how much I hate having bad seats. If I have to sit next to some greasy-handed person spilling their popcorn on me I will be irate."

"I don't doubt it." Dan follows her into the little independent theater. They head directly for the theater the movie is in and take their seats in an unoccupied row. "I told you it wouldn't be crowded. Do I need to remind you that not everyone is as particular as you about their seats to show up a full 45 minutes early?"

"40 minutes, given that you were 5 minutes late." Blair corrects and pulls down the armrest between them.

"So what do you suppose we do for the next 20 minutes?" Dan points out the stretch of time they now have to fill until the trailers start.

"What we always do, you tell me what you've been doing lately and I judge your lifestyle choices and then I tell you what I've been doing and you judge mine."

"Haven't I've been lectured enough today? First for my tardiness and then now for who knows what, maybe for choosing to eat again at the same Thai restaurant last night."

"Fine, we'll jump to mine. I broke things off with Finn."

Dan lets out a breath, "Finally. That guy was the worst."

"Tell me how you really feel," Blair rolls her eyes. "He wasn't that bad."

"Blair, his name was Finn. I mean, who willingly goes by that name?"

"It's short for Finley," Blair says in an obvious tone. "Anyways, aren't you going to ask why?"

"Hm," Dan strokes his chin, "He's leaving the East Coast to head west and study marine biology?"

Blair is unamused, "That's the best you can come up with? Your wit isn't nearly sharp enough today. Since you aren't going to ask, I will just tell you." She sounds irritated. "He texted me 'What's cooking good looking?' It ended right there and then."

Dan bursts out laughing. "Okay, that is truly terrible. Even if he wasn't laden with a multitude of other flaws I would still encourage you to stop seeing him just for that."

Blair tilts her head, "I know. Did he see that on an apron and think, hm Blair will enjoy that greeting?"

"Apparently. Good call on kicking him to the curb. I approve." Dan nods vehemently.

Blair smiles, "Glad to hear it. Oh, look trailers are starting." She pokes him in his side, "See we didn't have to wait 20 minutes, you're so dramatic."

Pushing open the theater doors, Dan and Blair walk out to the city only bathed in streetlights. They pause on the sidewalk and Blair says, "I have to admit, that was better than I thought it would be. Actually, it was a solid movie."

"Wow, that's like a glowing review coming from you." Dan says and then softens his tone, "I'm glad you liked it too though."

"So I'll see Sunday." Blair says before she hails a cab.

"Of course, if you missed waffle Sunday I would be concerned."

"Actually, I think Rufus would be the one most concerned. Wasted waffles are the bane of his existence."

Spotting a cab, Blair steps off the curb and waits for it to come to a stop before climbing in.

Dan forgoes going back to his apartment and heads to the loft after to have dinner with his dad.

"You decided on Italian after all." Dan says as he walks in and is surrounded by the aroma of garlic.

"You can never go wrong with spaghetti and homemade marinara. How's my favorite son?"

"Good!" Dan says enthusiastically.

"What'd you do this evening?"

"Movies with Blair." Dan replies as he piles his plate with noodles and sauce.

"Didn't know an outing with Blair Waldorf could leave you so chipper. Don't you two thrive of turmoil?"

Dan rolls his eyes, "We get along 90 percent of the time."

"50 percent, I'd say."

"Fine 80. Anyways she finally broke it off with Finn so I am indeed in a good mood after hearing that news. I hated that guy." Dan shakes his head.

"So you've said before." Rufus eyes him curiously Across the table as he scoots in his chair. "Actually, that reminds me, I've noticed something."

Dan looks up from his plate, "What?"

"It's just that it seems like you never like any of Blair's boyfriends."

"Actually Finn didn't make it to boyfriend status, luckily." Dan points out as he winds up spaghetti around his fork.

"Exactly. That's what I mean," Rufus says animatedly "Why wouldn't you want Blair to have a boyfriend?"

"It's not that, I just don't want her to date some guy I can't stand."

"I think you're missing my point. I can't recall you ever liking a single one of her boyfriends and I'm starting to wonder if there's a reason for that."

Dan narrows his eyes, "What are you implying, Dad?"

"I'm not implying anything, just making an observation." Rufus shrugs and resumes eating his spaghetti. He doesn't bring it up again but the conversation lingers in Dan's mind for the rest of the night.

The rich, caramel scent of maple syrup wafted through the loft as Rufus began serving breakfast to Blair, Dan, and Jenny who were seated around the table. After he finished dishing up the waffles, Rufus took his seat across from Dan.

"So Blair, how have you been?" He asked, instantly sparking skepticism in Dan.

"Well, you?" Blair replies.

"Never happier than on Waffle Sunday. So how's Finn? That's his name right?"

Dan glares at his dad from across the table, not liking where this is headed.

Blair seems surprised by Rufus's mention of Finn but replies with zero skepticism. "I wouldn't know. We aren't seeing each other anymore."

"I bet Dan's relieved," Jenny joins in the conversation, further irritating Dan. "He hated that guy."

"So he told me about a million times." Blair rolls her eyes. "He wasn't that bad. I mean for someone who made quite a few questionable choices in dating he certainly is openly opinionated."

"Ah," Rufus says, eyes sparking with mischief. "Who are you referring to?"

Dan begins trying to telepathically send the message to his dad to stop immediately.

"Hmm," Blair tilts her head as she thinks. "Autumn was pretty insufferable. I mean, every time she saw me with a cup of coffee she told me it would give me cancer."

"She said that one time." Dan can't help but be defensive.

"Well if it wasn't about coffee then it would be about the toxins in my nail polish or the chemicals in cleaning products Dorota uses. She was the literal definition of fear mongering."

Jenny jumps in, "I agree with Blair. It was totally annoying. I mean, she literally tried to take out my hair extensions without my permission because she said it was damaging my hair follicles. Like, hello, are you my hair stylist? I don't think so, get your hands off my scalp!"

Blair laughs, "See, told you." She says to Dan. "Insufferable."

Jenny nods in agreement.

Suddenly, Blair's face lights up. "Oh but I almost forgot about one of his most unfortunate choices." She pauses for effect, "Pyramid Piper."

Jenny bursts out laughing "Oh my god, you're so right. Remember when she brought over all those candles to Waffle Sunday?"

"Or that time she walked in and stocked the juices in the fridge during Waffle Sunday, left an order form for us to refill when we ran out, and then just left? She hadn't even been invited over yet took it upon herself to come on in. Stalker status." Blair shakes her head.

Dan gives his dad a look to say, _see what you've started?_

"I mean how many pyramid schemes can one person be involved with within the span of three months? She must have broken some sort of record." Blair muses.

"Okay, Blair," Dan can't stop himself from saying something. "It's not like you haven't had a number of poor choices in dates. Didn't one guy take you to the Jersey Shore to 'widen your horizons'?"

Blair wrinkles her nose, "He tried to and I obviously did not go and then, promptly stopped seeing him. Unlike you, I know when someone's a dud. By the way, Rufus, you've been awfully quiet," At Blair's words, Dan feels a flood of relief. She's finally catching on to her dad's scheming. "Certainly you must have some input."

Dan visibly sags in disappointment. That was not the direction he had hoped that was headed in.

"Well, I think the two of you have a rather interesting collective dating history. I find it most interesting though, how little you two approve of one another interests when you are best friends."

"Best friends? I think that's a strong word choice. Dan, don't you agree?"

Dan nods.

"Well then, close friends," Rufus amends. "But it's a fair choice."

Blair shrugs. "I guess the real issue is that I chose to be friends with someone who has a terrible taste in romantic pursuits."

Dan narrows his eyes and then lets out a breath. "Well, I think that's enough walking down memory lane for one breakfast, don't you?" Then he quickly changes to subject onto Jenny's classes and the conversation is temporarily forgotten.

After breakfast, Blair and Dan head to his apartment to watch a movie. As soon as they are through the door Dan turns to Blair, "Did you have to give in to my dad's little scheme so easily?"

Blair's brow creases in confusion, "What do you mean?"

Dan exhales loudly, "Seriously? The whole exes thing was just to prove a point."

"Oh, he was awfully nostalgic this morning. What was that about?"

Dan debates whether or not to tell her but relents, "He said that you and I always find issue with each other's romantic choices."

"He's not totally off base with that remark," Blair says as she sets her coat down on the bar stool and then leans against the counter.

Dan runs a hand through his hair, "He implied, to me, that there's a reason for that."

"What reason? You have terrible taste and should hire a matchmaker? I could get on board with that."

"Blair," Dan is getting irritated. "The implication is that we don't like one another's choices because…" He can't bring himself to say it.

Realization washes over Blair's face, "You like me? Is that what you're saying? You like me and you don't want me to date-"

"No," Dan interrupts her. "I don't, don't flatter yourself."

Blair looks taken aback.

"That's just what my dad thinks," Dan continues. "He thinks we secretly like each other therefore we don't want each other dating anyone else."

"That's ridiculous," Blair says automatically.

"That's what I said but you going on and on about how terrible all my exes are didn't help to disapprove that notion."

"Well, how was I supposed to know that's what he was up to? You could have tipped me off."

"I didn't realize he would bring it up again." Dan hesitates before saying, "Anyway, I've been thinking about it and what if he's right?"

Blair laughs, "no way."

"But Blair, we can't name one ex that we didn't have a problem with."

"So? I don't think we should subject ourselves to analyzing his little theory."

"Why not?"

"It's like opening Pandora's box, there are only two possible outcomes. A) one of us discovers we do in fact like the other or worse yet _love_ while the other realizes B) they have zero romantic interest in the other because of X qualities the other possesses and now they can't stop thinking about all those qualities they don't like. So inevitably we stop being friends."

"What if both of us reach the same conclusion?"

"It still ends either way."

"Even if both of us reach outcome A?" Dan can't bring himself to say like or love each other.

"Yes, it'd be destined to fail." She says in an obvious tone. "Because then there would be all this pressure to turn our friendship into something more. If it ends, then not only does the relationship end but also the friendship" Blair wrinkles her nose and shakes her head. "It's a bad idea, in fact, I think we should stop discussing this to be safe."

Dan thinks over what she says, "If that's what you think is best." He heads over to the TV to switch it on and start the movie. "Can I just ask you one thing and then we close the subject?"

Blair shrugs. "I suppose."

"Have you ever thought about it? About us?" Dan says, surveying her from across the room.

Blair doesn't respond right away and when she does, she reflects back the question. "Have you?"

"Not until today," Dan says which isn't exactly a lie.

"Me neither." Blair says matter-of-factly. "So, what are we watching?" Her question signaling the end of the conversation.

* * *

 **I hope you all like the concept of this story! I wanted to try something a bit different from what I've written before. So I figured writing from Dan's perspective would be a change and also having Dan and Blair already be friends would give them a different dynamic from my other stories. This story will also be interlaced with flashbacks so you'll get to see how Dan and Blair become so comfortable in their friendship.**

 **Expect another update tomorrow :)**


	2. Chapter 2

Three Years Ago

Dan walks into the bustling museum, scanning for Serena's shiny blonde locks of hair. She almost always stands out with her height and charisma. But instead, his eyes lock on a doe-eyed brunette with a wary expression. Serena is nowhere in sight. He resigns himself to greeting Blair since it's not like he can pretend he hasn't seen her until Serena arrives. He approaches her hesitantly from across the museum foyer.

When he reaches her, he doesn't want to be the first to speak. Luckily, Blair speaks first, "Where's Nate?"

"He had to sub in a lacrosse game so he's not coming. Where's Serena?" He can't help but glance around again.

"Not coming. Claimed she totally forgot she told Walter she would have brunch with him." Blair's tone was filled with disapproval and annoyance.

"Who's Walter?"

"New boyfriend."

"So it's just you and me?" Dan does a third scan of his surroundings, hoping to be proven wrong by the sight of a familiar face. Not seeing one, he turns back to Blair who he learns is doing the same. "I can see you're scanning for exits. Go ahead."

Blair faces him again with a lift of her chin. "I am not. I will be following through on my plans. In fact, I've been looking forward to seeing this particular exhibition despite the less than ideal company." She wrinkles her nose slightly.

"Oh so now you're going to stay to prove me wrong?" Dan says with a wry smile.

"No, nothing to prove. Are you coming or leaving, Humphrey?" She says, starting for the entrance.

Dan follows her, in disbelief he is subjecting himself to a day at the museum with Blair Waldorf.

"How was the Degas exhibition?" Rufus asks when Dan enters the loft later that afternoon.

Dan shakes his head, almost disbelieving himself. "Interesting to say the least. It was just me and Blair."

Rufus laughs as though Dan has just said something hilarious, "Not Blair Waldorf?"

"The one and only." Dan heads to the kitchen to pour himself a drink.

The smile disappears from Rufus' face. "Wait, you're serious."

Dan nods as he takes a sip of his already full glass.

"You willingly hung out with Blair Waldorf?" Rufus asks incredulously.

"I wouldn't so much as call it hanging out as more so was in close proximity with. Wait, actually, that sounds worse. Maybe, abide is a more appropriate term." Dan muses this.

"Didn't you once call her, and I quote, 95 pounds of girly evil?" Rufus's eyes are inquisitive.

"Yes, but she's actually, not that bad." Dan surprises himself by saying and then continues, "And what were we supposed to do? Both be at the same museum, exploring the same exhibition and pretend we don't know each other? That's way more awkward."

Before Rufus can answer, Dan hears his sister's door open. Jenny strolls out into the living room a moment later, "Hey just realized you're here. I was actually just reading about you."

Dan's looks around to be sure she means him but her eyes are fixed on him. He then points to his own chest, "About me?"

"Yeah, I saw on Gossip Girl you were with Blair Waldorf?" She says it like a question, the same expression Rufus had is on her face too. "Were you on a date? Because that's what Gossip Girl is reporting."

Dan's eyes widen, "What, no of course not. We just… were at the museum together."

"So you're friends with Blair Waldorf?" Jenny says slowly.

"Why is everyone so concerned with this? Blair and I share mutual friends so I suppose we are acquaintances. Our friends flaked on us so we were happened to hang out alone. It's not that big of a deal."

"Okay, Dan." Jenny says sarcastically and laughs. "Good luck convincing the whole of the Upper East Side of that. Gossip Girl's photos are pretty incriminating…" Jenny's tone is chilling so that the hairs on Dan's arms stand on end. He avoids Gossip Girl the rest of the day, and after every subsequent encounter with Blair.

* * *

 **Glad to hear you guys like the concept so far! Every other chapter will be a flashback. So the next chapter will be back to the present :) Thanks for reading and reviewing! Next update will be this weekend!**


	3. Chapter 3

Dan drums his fingers on his desk. He has a freelance assignment due to his editor at 5 pm, just a few hours away but he can't bring himself to write it. He tries to focus on it but his mind keeps wandering to his conversation with Blair yesterday. The way she didn't hesitate with saying she hadn't thought about them. Certainly, she must have at some point, right? But the way she said it, told him otherwise.

He felt angry with his dad for even bringing it up. Like Blair said, it was a dangerous topic. Now, he was analyzing their friendship and reading into things that he shouldn't be. Where their friendship had once been easy, it could now potentially be tenuous.

What he kept thinking about the most, is the _what if?_ What if he had told her the truth when she turned the question around on him? Would she have said the same? He hated himself for not being brave enough to tell her the truth. At the same time, he knew she was right. Discussing a possible romantic connection between them would mean navigating through dangerous territory. It was a topic better left closed.

By Wednesday, Dan was just going through the motions as the week dragged on. Not giving it much thought, he headed straight to the loft after work. Upon opening the door and smelling the maple and oak aromas of his dad's dwelling he was relieved to sink back into the couch.

"Dan, what a surprise. Don't you usually hang out with Blair on Wednesdays?" Rufus asked as he emerged from the bedroom where Dan had heard him strumming his guitar.

"Oh yeah," the thought just struck him he hadn't seen or talked to Blair in days. Usually, by midweek they had been to a movie together, tried a new restaurant, and experimented with new cocktail recipes at Dan's place. "I guess I forgot." He shrugged.

Rufus eyed him but said nothing. He headed back to his room and returned a few moments later with an instrument in each hand. He handed Dan a metallic navy electric guitar and took the well-worn acoustic guitar. Without a word, the two began strumming the familiar tune of Lincoln Hawke's best-known song.

Dan had forgotten how the simple act of playing a few chords could stir him from his melancholy. Afterward, Rufus finally mentioned Blair. "Weren't you two going on about some wine bar opening this week?"

Dan remembered then that she had reserved them spots at the opening of La Vie en Rosé, a chic new wine bar in Soho. He nodded, "She was going on about it, not me. I just am along for the ride, the alcohol helps though."

Rufus laughed, "Along for the ride... I think that actually sums up your friendship."

Standing outside the wine bar on Friday, Dan checked his vintage leather watch again and cross checked the time with that of his phone and saw indeed it was ten past. His eyes were fixed straight ahead on the still empty sidewalk. She was late or not coming. Given that she once claimed being later than five minutes for a scheduled one on one hangout would tarnish her reputation, he figured she wasn't coming. He thought they were fine since they had both decided not to discuss Rufus's implications any further but apparently not. He was about to leave when his phone rang, he saw her name on the screen. At least she had the decency to call and cancel, even if it was late, he thought to himself.

"What's your excuse?" He said as he answered.

"Huh?" She sounded both confused and irritated. "What's yours? You're fifteen minutes late, a new record for tardiness."

"You're the late one. Don't try to fool me, I'm already here." Dan could just picture her in a cab, thinking she outsmarted him.

"No, I'm not." She said in an obvious tone. "I've been inside for 25 minutes."

"You're inside?" Dan peered inside the window. "No you're not, I looked and you weren't." He turns back to face the sidewalk. "I'm outside." He adds.

"Well, could you do me the great service of coming inside now?" She said sarcastically.

Dan shook his head and headed in. He left the phone on the line, prepared to not see her. But then he spotted her shiny tendrils of hair cascading around her shoulders. She was tucked into a secluded corner booth and clicked the phone off when their eyes met.

He slid into the rustic bench across from her. "Hey," he said nonchalantly.

"Why the fuck were you outside that whole time? Were you trying to test me?" She glared before returning her eyes to the drink menu.

"Obviously I didn't know you were in here." Dan shakes his head. "Let's get you a drink, you need it."

"Seriously, hanging out with you always requires a drink." She looks up and her smile that tells him she's joking. The waiter comes over and takes their orders.

"So how have you been? Haven't talked you to in a few days." Dan asks when their drinks come.

Blair sighs, "Ugh, you would not believe my week. I spent 80 percent of my week dealing with incompetent vendors who can't get our fabric orders processed. Then, the other 20 percent was spent trying to cancel this ticket to Tuscany which was intended for Finley but obviously won't be needed. But it turns out it's definitely non-refundable." Blair reaches into her purse and retrieves an envelope. She slides it towards him. "So, I suppose you have no other choice but then to join me."

Dan stares down at it. "You want me to come to Tuscany with you? To your dad's wedding?" He says disbelievingly.

She nods. "It'll be fun. Actually, Serena's in Europe too right now so I'm trying to convince her to come. It can be a little reunion of the Three Musketeers."

Dan laughs, "Remember how long that nickname lasted?"

"Like 5 minutes despite Serena's determination." Blair's laughter fades. "Seriously, will you come? The dates are on the tickets." She gestures towards the envelope.

Dan hesitantly takes it. "I'll see if I can get work off. No promises though." Dan drinks from his glass of wine.

Blair beams, "I'll take that as a yes. Now I just have to get the villa situation sorted out. Obviously, they'll have to adjust the room to have two double or queen beds because I am not sharing a bed with you. Even I have my limits. Sharing a villa, that's fine, sharing a bed..." She shakes her head. "Well, I think that would give Rufus way too much cannon fodder. Don't you?"

Dan sputters on his wine. He clears his throat, "I agree. That will most definitely need to be fixed." He can't help but wonder if sharing a villa with Blair is entering Pandora's box itself.

* * *

 **Note: Dan is a journalist and Blair works for Waldorf Designs. Sorry, I'm using these jobs again like in my other stories but I think it just works well for their characters. This story won't delve into their work lives so I wanted to keep it straight forward. Hope you all are still enjoying it! Expect another flashback chapter tomorrow or Monday :)**


	4. Chapter 4

**So happy to hear you guys like the story so far! Thank you so much for leaving reviews and feedback :) Quick note on the flashbacks, they are all in chronological order. I'll update again by Wednesday evening. Thanks for reading!**

* * *

Three Years Ago

Dan and Blair stood off to the side, both enrapt in people watching. They were at a charity silent auction accompanied of course, by Nate and Serena. Both of their friends were far more interested in bidding than either of them. It struck Dan then how similar Nate and Serena were. They both often had expressions of childlike wonder on their faces, were easy going, and charmed those around them.

Blair leaned in suddenly, the slightest trace of Chanel No. 5 wafting along with her. She whispers, "What do you want to bet Serena bids on jewelry worn in a movie or by a celebrity?"

"What do you want to bet Nate bids on a yacht or sailboat?" Dan counters.

Blair sticks her well-manicured hand out, "Deal."

Dan takes her hand and shakes it firmly. "Our friends are so predictable."

"What if we both are right?" Blair asks as the thought seems to strike her. Her eyes narrow, "Also, what exactly are we betting on?"

Dan thinks for a moment. An idea forms, "If I'm right, you go with me to the typewriter exhibit I told you about."

Blair wrinkles her nose, "Ugh, I better get my oversized cardigan and wide-rimmed glasses ready. That's bound to be hipster central. But fine."

"And if you win," Dan continues, "I go to one fashion week show of your choosing."

Blair seems delighted by this idea and he watches her stifle a laugh. "Deal."

"If we're both right, then we do both." Dan finishes.

Blair gives him a rare smile and compliment, "Good plan Humphrey. I must say I am somewhat impressed."

"Guys, look at this!" Nate exclaims. Both Dan and Blair turn to see what he's looking at. Nate leans forward and reads from the poster, "The SS Recess: Your sea-set home away from home. How much should I bet?"

"Don't worry Waldorf," Dan looks over at Blair as Nate scribbles down a number. "We'll go to Urban Outfitters before the exhibit."

"That's not even a good boat name," Blair says, unamused. "He should rename it." Dan watches her eyes flick towards where Serena stands, reading something. "What are you looking at, S?" She asks, innocently.

"A 14-carat gold serpent cuff worn by Elizabeth Taylor in Cleopatra." She says in awe. She starts to pick up the pen next to the bid sheet.

"Our friends are tragically predictable." Blair sighs.

"I bet that'll go for a lot. Probably more than all the Louboutins in your closet, combined. Safer not to bid." Dan says to Serena in his most earnest tone.

Blair jabs him with his elbow. "Cheater." She walks over to Serena. "Wow, so gorgeous. I mean, you have to bid on it right? It would be a crime not to."

"True." Serena writes down her bid. Blair turns back and gives Dan a wicked smile.

Once she's near him again, she says, "I'm sort of thinking a Kate Spade show might be perfect for you. It's presentation style so you'll actually have to walk around the room to see the full collection. That way you can truly be present. Oh and we can stop by Jack Spade first to get you all preppy for the show. We can coordinate outfits."

"I can hardly wait." Dan's lack of enthusiasm elicits a beaming smile from Blair. He realizes then with surprise, that the idea of hanging out with Blair alone doesn't actually horrify him. It was odd to think how just a couple of weeks ago, he would run from any solo encounter with Blair Waldorf. How at the museum, he had nearly fled when he saw just her. But now, he didn't dread it at all. Not one bit, in fact.


	5. Chapter 5

**Sorry for the delay in updating! I had hoped to yesterday but got so busy I didn't get a chance until now. I will update with another flashback chapter by Sunday. Thanks so much for reading, reviewing, following, and favoriting! I'm so so happy you all like the story so far :)**

* * *

"Does this mean you're going to make me go suit shopping again?" Dan groans as Blair sips her latte across the table. He quickly learned that there was no backing out of this trip once the idea formed in Blair's head. By Saturday afternoon, Blair had roped Dan into attending her father's Tuscan wedding by emailing him an itinerary complete with flight, accommodations, and day-to-day activity details. Apparently, she was unsuccessful in arranging separate villas but did manage to get them a two bedroom one so at least they will have their own rooms.

Blair seems to ponder this and then eyes him. Dan feels a bit self-conscious as she leans slightly forward and scans him from head to toe. "You look to be just about the same size as two years ago. So the blue suit will do. It is a very fine suit if I do say so myself." She says with a satisfied smile.

"Of course you do." Dan remembers her fretting over fabric swatches, cuts, trims, and all the most minute of details when it came to that suit. She had her mother's designers custom make it for him and waved off his protestations.

"So you'll wear that the night of the wedding. As for the rest of the outfits, maybe I should help you pack…" She wrinkles her nose. "I can't be seen with you in Tuscany wearing that." She gestures at this crinkled flannel.

"I can pack myself, Blair." Dan says defensively.

"As long as you promise me no plaid."

"No plaid." Dan agrees because if that'll keep her from coming over and rifling through his drawers than it's worth it. He might just have to go shopping though for some non-plaid button downs. "So is Serena still coming too?"

Blair rolls her eyes. "That remains to be seen. You know her, it's impossible to lock her down for anything. Everything has to be on a whim."

"True… It would be nice to see her again. It's been.." Dan tries to think of when he last saw her.

"Too long." Blair says in an exaggerated tone. "Not since Christmas."

"That's right." Dan says recalling the Christmas reunion they had at the Waldorfs. That was actually the last time he saw Nate too, he realizes.

Blair finishes her coffee and makes to stand. "Ready?" She asks and Dan nods. "I have to head off now to Barneys and pick up some last minute items. I suggest you do the same. You have exactly four days Humphrey to get yourself in order before we leave. I'm serious about the ban on plaid."

"I know you are." Dan says and shakes his head.

"Good." She waves him off and then hails a cab, climbing in gracefully.

He can't bring himself to tell his dad in person that he's going on this trip with Blair. He knows exactly what look his dad will give. Instead, he decides to text him in a nonchalant manner. Even though he knows that it's not certain Serena will go, he decides mentioning her presence will perhaps ward off any implications of anything between him and Blair happening.

After firing off the text, he heads to Maison Kitsuné which is hipster enough that it still suits his style but high-end enough that Blair will be pleased. He feels somewhat annoyed with himself for making such an attempt to please but proceeds on. After perusing the well-curated Parisienne-originated store, he decides on two oxford shirts; one in blue and one in white, and a check shirt because she didn't say no checks, just no plaid. It may look similar but it's his small protest to conforming completely.

For the next few days, as the trip rapidly approaches, he can't help but feel a twinge of something every time it crosses his mind. Specifically, when he thinks of sharing a villa with her there's a flicker of… something undefined that makes him uneasy. So uneasy in fact he thinks of canceling multiple times. But then he thinks of how furious she will be and that he will have to go 5 days without seeing her. The dismay at thought wins out every time he has the internal debate.

So he indeed finds himself boarding a red-eye flight with Blair and a massive load of carry-ons that she makes him carry, of course, on Thursday night. As he walks through the jetbridge he almost glances back but resigns himself to the fact that there is no turning back. So he carry's on following the clicking sound of Blair's patent pumps and her bobbing head of curls. She glances back and smiles at him as they wait to climb into the plane and he does his best, to annoy the flicker that passes again.


	6. Chapter 6

**I started working on the next present-tense chapter so I'm hoping to have another update this weekend. Also, I got a fun Dair story idea that I think I'll try out. So far all I have is the title which would/will be Blair Waldorf Does Not Camp. The two of them would be a couple in it and basically comical antics would ensue on a camping trip. Let me know if you're interested in reading that and I'll get started!**

Two and a Half Years Ago

Standing on the jetty and feeling the cool breeze against their solemn faces, the trio watch as Nate's sailboats glides off towards the sunset. All they can see now is his silhouette and they watch in silence for a while until he's nothing but a speck on the horizon.

Serena is the first to break the silence. "Well just the three of us now, I guess." She musters up a cheery smile and wraps her arms around both Dan and Blair. "The three musketeers!"

Dan watches as Blair wrinkles her nose and tries to shake out of Serena's grip. "Ew, no. We are not calling ourselves that." She manages to wriggle out and then crosses her arms defiantly.

Serena drops her arm from around Dan and says, "Fine, you two are no fun." She sighs, "How am I going to manage without Nate? I can't deal with how seriously you guys take yourselves."

"I don't know, S. Maybe you should be sailing around the world with him if our company is so miserable." Blair retorts.

Serena smiles, "No, I'm glad I'm staying. Besides your friendship would not survive without me." She looks between Dan and Blair. "I'm basically the glue that holds this group together."

Dan interjects, "Are you really though? I would have thought Nate was."

Blair nods, "Same, I think it's Nate."

"Seriously though," Serena ignores Blair and then says. "What should the three musketeers do now?"

Blair and Dan look at each other at the same time with matching expressions. They are silently communicating, _Is she seriously going to insist on calling us that?_

Blair's face suddenly lights up, "Let's go to that modern art pop-up in Chelsea."

"I wanted to go to that. I heard some works by Marguerite Humeau will be on display." Dan says with enthusiasm.

Serena groans, "Nooo, not another boring art thing. You two are always dragging me to those. I veto that suggestion."

"Two against one," Blair says with a bright smile. "We outnumber you now." She links her arm through Serena's. "Come on S, we'll go to Serendipity after just for you."

"I'll go if you two promise to go with me to the silent disco next weekend." Serena counters.

Dan can see Blair contemplating this. He can just imagine her weighing the pros and cons of the deal. On one hand, he could see Blair liking the independent experience of a silent disco. On the other hand, he can see her turning up her nose at the smell of weed and hippies who are bound to be there. She looks to Dan with a questioning expression and he gives her a small nod of encouragement. She sighs loudly then says, "Deal."

Two hours later, after deciding they have tortured Serena enough at the pop-up, they find themselves sitting in a booth at Serendipity. Each clad of them with a frozen hot chocolate with Serena sitting across from Dan and Blair. Blair is eyeing Dan's frozen hot chocolate and then suddenly exclaims, "Yours has more whipped cream than mine. Trade me." Before Dan can say anything Blair swaps the two old fashioned sundae cups.

"Blair!" Serena protests. "All you do is boss poor Dan around."

Blair smiles sweetly and leans in slightly towards Dan. She playfully leans her head on his shoulder, "He loves it though. Don't you Dan?" She lifts her head and then dips her spoon into what was formerly his frozen hot chocolate.

Dan just rolls his eyes. "She has her moments. Also, I only let her switch those because this one has more caramel syrup."

"Whatever," Blair shrugs refusing to show any unsatisfaction. "This one is better."

Serena smiles and shakes her head ruefully. "I miss Nate already but at least there's never a dull moment with you two, save for the art exhibits."

Later, Dan finds himself thinking about that remark Serena made. That he and Blair wouldn't be friends anymore if Serena left too. At the start of the year, he would have completely agreed. But now, he wasn't so sure. If anything he and Blair had grown closer over the past six months, to the point where he would consider her a closer friend than Serena. The two of them had now hung out at least a handful times without Serena or Nate. Actually, he thinks, only being able to count on one hand the number of times you've hung out one-on-one with someone probably isn't the strongest proof of a lasting friendship. But still, it's something.


	7. Chapter 7

**This was quite the tricky chapter to write given it needed so many transition scenes so apologies for the delay. I ended up scrapping it and then rewriting it so I really hope you like the finished result :) Next update will be this weekend! Thanks so much for reading and reviewing!**

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Dan opens his eyes to see sunlight flooding into the cabin of the airplane. After adjusting his eyes, he changes his monitor screen to show the flight progress and sees they are only an hour from landing in Italy. He glances over at Blair who's still sound asleep. At some point during the flight, she put on her sleeping mask which is identical to Audrey Hepburn's eyelashed-turquoise mask in Breakfast at Tiffany's. Her head is turned towards him and she has the slightest smile playing at the corners of her lips. He contemplates waking her but decides to wait until they are closer to landing.

Blair ends up waking up on her own half an hour later as the flight attendant announces their descent into Italy. "Good morning," Dan says as she sits up. "Or I guess, good afternoon. It's noon here."

Blair runs a hand through her hair, "I can't believe I managed to sleep through the whole flight. Did you?"

Dan nods, "I only woke up a bit before you."

"Good," Blair is back in full travel mode already. She's straightening her itinerary which got a bit crinkled during the long journey. "So we'll head straight the villa, unpack, and then eat. Does that work for you?"

"Of course." Dan appreciates her pretending to give him an option even though he knows she had the afternoon planned out on the itinerary already and would be unlikely to deviate.

It's 1 in the afternoon by the time they check into their villa. The villa is one of 12 that make up the property Harold and Roman rented for the wedding. The whole property is astoundingly luxurious and their villa is just as impressive. The exterior is stone and surrounded by well-tended gardens. The interior holds a massive living room, kitchen, a master bedroom and guest bedroom each with their own bathrooms.

After taking in the accommodations, Dan deposits Blair's luggage next to the armoire in the master bedroom and then places his own in the guest. Dan exits the room to find Blair opening the double french doors which lead out into their own private pool and jacuzzi which is enclosed by a garden.

"This place is insane." Dan says as he approaches her.

"I know, it's nicer than I was expecting. It looks like we got quite the upgrade by switching to the two bedroom." She gestures to the pool and jacuzzi. "We wouldn't have had that with a one bedroom."

"Good thing we got swapped then. That would have been unspeakable." Dan says in mock horror.

Blair laughs, "Definitely. We would have had to demand a change in accommodations." Blair echoes his tone.

"Now what?"

Blair shrugs. "We're supposed to go to see the David in Galleria dell'Accademia. But it's hard to leave this." Blair sighs. "But we should go. I mean, you can't be in Florence and not see the David right?"

"Unless you're Serena.'

"Or Nate." Blair adds as they walk out the door.

They spend the afternoon playing tourists. Surprisingly, Blair doesn't complain once about the sweltering heat or the crowds. In fact, she seems more relaxed than Dan can recall seeing her in a long time. What's most surprising is how at ease Dan feels. He thought it might be weird traveling with Blair but it's not. It's just as though they were at a museum back in New York. She knows exactly what he means every time he expresses a view on a work and respects his ideas. Past girlfriends mock his commentary as they walked through museums but Blair never has.

As the sun begins to lower and emit a gold glow, Blair and Dan exit the museum. Blair immediately suggests gelato to which Dan obliges. Blair surprises him yet again by speaking Italian to the girl at the counter. She insists she isn't fluent but she seems more than practiced with the foreign language. Dan notices the girl seems to be indicating him and she giggles slightly.

"What did she just say?" Dan whispers to Blair, feeling out of the loop.

"She said you need a haircut." Blair replies as she takes a bite of the sample of strawberry gelato.

Dan gives her a reproachful look.

"Fine she didn't say that." Blair amends. "She said we make a beautiful couple."

"Oh." Dan says awkwardly, wishing he hadn't asked. He flinches as Blair suddenly links her arm through his.

"What are you doing?" He hisses in hushed tones.

"I don't know how to explain in Italian that we're not a couple so might as well go along with it." Blair shrugs and then smiles at the girl and points to another flavor to sample.

As soon as they're armed with their gelato, Dan shakes his arm away. "No need to keep the charade up anymore." He says when she looks questioningly.

"Whatever, that got me this for free." She holds up her spoon in triumphant.

Once they're back at the villa, Dan heads into his room to change for dinner with Blair's family. He puts on the Maison Kitsune shirt and dark jeans with a pair of chukka boots. Glancing in the mirror, he straightens his collar before heading out into the living room.

Blair appeared ot be in the process of applying lipstick but he watches her reflection nearly drop the lipstick as her eyes scan him. She whirls around, "Humphrey, I am impressed." She steps forward and reaches out, feeling the fabric of the shirt. "Is this from Maison Kitsune?"

Dan feels self-conscious runs a hand through his hair. "Yes. As you said, no plaid."

"I love it." Blair breathes. "I knew you had good taste if you would just try a little harder."

Dan regains himself, "Glad to hear you're pleased."

Blair turns back to the mirror and finishes painting on a wine shade of lipstick. Once she's done, she leads them out to the terrace where a large dining table sits. The table is decorated with garlands and a burlap table runner. Most of the guests are already seated and so are the hosts, Harold and Roman. Spotting his daughter, a wide smile sweeps across Harold's face. "Blair Bear!"

Blair embraces him tightly and kisses him on the cheek. "Dad, you remember Dan right?"

Dan extends his hand and Harold gives him a warm handshake. "Of course, I couldn't forget my daughter's best friend. Dan, I'm so pleased you could join us this weekend."

Throughout dinner, Dan and Blair chat to Harold and other various Waldorf's. Blair always makes sure to introduce Dan and make sure he is properly introduced. As much as he enjoys the evening, he's happy for the respite from chatter as they finally return to their villa. It's past 10 so Blair suggests they go to bed to try to adjust to the time change.

But lying in bed, Dan struggles to fall asleep. He reasons it must be due to the fact that it's still 4 in the early evening in New York. Plus, that cappuccino he had this afternoon probably didn't help. After tossing and turning for half an hour, he climbs out of bed. He heads into the living room, hoping to go out the french doors to get fresh air outside. But he sees Blair is already out there.

"Hey. You couldn't sleep either?" He says as he steps outside.

"No. So much for my plan to not be jetlagged tomorrow." Blair turns away from the garden, facing him. She walks over to the pool and sticks in her bare legs. She's wearing a satin pajama set and the fabric gleams in the moonlight.

"Is it heated?" Dan sticks his hand in. "It's the perfect temperature."

"We should go swimming," Blair announces. "I mean, when else will we? We might not have time tomorrow with the rehearsal. Then, Sunday's the wedding. Plus, we're both up."

"Now?" Dan says in confusion.

"Yes, now. I hope you packed swimming attire." She says as she shakes the water off her legs.

10 minutes later, Dan is wading into the cool water. Blair follows and takes each step one at a time. "It's heated, why are you shivering?"

"I have to adjust," Blair says in cutting tones. "Just go on. You're rushing me." She folds her arms across her bikini-clad body. The suit is a retro style with a halter neck and floral print.

"It's worse if you go in slowly, just come in all the way."

Blair shoots him a withering glare.

"You are the one who suggested swimming." Dan points out.

Blair exhales loudly and then submerges herself and water, not getting her hair wet though. "I suppose it's not terribly cold."

Dan laughs. "It's heated water, I would say not."

Dan swims to the side of the pool and rests his arms on the cold tile surrounding the pool. Blair joins him a moment later and lays her head on her arms facing him. "I'm glad you're here."

Her sudden sincerity catches Dan off-guard. "I am too." He says after a moment, really meaning it.

As they wade in the water, they talk about all the other parts of Italy they would like to see. Blair wants to go to the vineyards along the coast while Dan wants to see Brunelleschi's Duomo in the Florence Cathedral. As they each describe their imagined travels, Dan eventually feels the beginnings of sleepiness setting in.

He stifles a yawn, "I think I'm going to head to sleep."

Blair nods, "Me too." Once she's out of the pool, her relaxed face suddenly morphs into one of panic.

"What?" Dan asks, alarmed as he steps out of the pool.

"Shit, we forgot towels." She shivers slightly and then hugs her arms around herself.

Dan glances around and sees the stark lack of anything to even work as a towel. "Shit, you're right."

Blair darts for the door and Dan follows. She goes into the bathroom and he hears her say, "What the fuck?"

"No towels?" Dan heads inside his own to check and sees its towel-less too. He heads for the hallway glancing around.

"Where the hell are the towels?" Blair sounds incredulous. She comes into the hallway and he can hear her teeth chattering as she turns off the AC on the temperature control.

"Found them!" Dan exclaims as at last, one of the closets he opens is full of linens. He retrieves two towels and proffers one to Blair.

She immediately wraps herself in it and sighs in relief. "I knew spontaneity didn't suit me." Blair says as she hugs the towel even tighter around her shoulders.

Dan laughs and leans against the hallway, drying himself off. "I think it does." He says, meeting her eye.

There is silence, neither of them breaking each other's gaze. Something about the way her hair falls over one eye and the way she's looking at him makes his stomach lurch.

"I guess I should go to bed." She says at last, not moving.

"Right, I should too." Dan says but stays steady where he stands.

Suddenly, the loud sound a clock chiming midnight rouses them from their stupor. Blair moves first, into the living room where the clock stands. "Okay, we need to turn that off. I can't deal with that going off every night we're here."

Dan shakes his head, shaking off that fleeting moment. "I didn't even realize it was so late." He stands there for another moment before finally saying, "Goodnight, Blair." He heads into his room, not looking back at her.


	8. Chapter 8

**I'm so glad to hear that last chapter was well-received! Thanks so much for the feedback :) Also, guests _J_ and _RF_ , thank you both so much for continually reading and reviewing! I appreciate each and every review, they mean so much.**

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Two Years Ago

As Blair descends the stairs of her penthouse, Dan left speechless. He's seen her dressed up countless times before but this time feels different. Maybe it's because he's the only one there right now to see, and that her eyes are trained on him. As she glides down the last step, she offers her arm for him to take. Silently, he links his arm through hers and tries to regain himself. Not able to meet her eye, he says, "You look beautiful."

"Thanks." She reaches her other hand to touch his lapel. "I see the suit worked out." She nods in self-satisfaction. She leads him into the elevator and presses the lobby button.

The elevator car ride is silent, with Dan rethinking the decision to come with her tonight. Throughout the past two weeks, he knew this night loomed yet somehow he never thought he would find himself following through. When Blair first suggested he accompany her as her date to her cousin's wedding he thought it was a joke. There was no way Blair Waldorf would want to take him, Dan Humphrey, as a date in such a public and romantic venue as a wedding. Even if she proudly calls him her best friend. But then he found himself at suit fittings and now, here. Unable to back out now. He could already feel the evening shifting their friendship towards something unfamiliar. Towards treacherous territory that he felt certain might break it.

But as the cool air of the late afternoon hits him once they pass through the lobby doors, he's faced with the realization there's no backing out now. So he blindly follows Blair into a situation that he feels confident will change everything.

Blair seems to be scrutinizing Dan as they sway slowly to the music. One arm is wrapped around him while the other gracefully holds his arm up. He supposes all WASPs teach their daughters to dance like this, elegantly and efficiently. While her posture is effortless and seemingly poised, her face is another story. Her porcelain skin is creased slightly at the brow and her eyes are fixed on him.

"What?" Dan asks finally, feeling self-conscious under her gaze.

"I just noticed, you have good bone structure," Blair says, casually. The crease leaves her face and the edges of her lips twitch up in a small smile.

"Thanks, I guess." Dan says in a skeptical tone. Then he adds, "So do you."

Blair laughs. "I suppose I am beginning to see a bit of the Humphrey appeal. In fact, you could do a lot better than the girls you date. You could definitely do way better than Patchouli Peyton." She drags out the word patchouli to emphasize her clear distaste.

"Do you have to nickname everyone I date?" Dan groans.

"Some of them are just asking for their nicknames." Blair shrugs. "I mean, does she bathe in dried rose petals and sticks of cinnamon?"

Dan shakes his head. "Well, I'm not seeing her anymore so perhaps you can lay off the scrutiny now."

"Fine." Blair agrees. "But seriously, you do clean up quite well and make a rather presentable wedding date."

Dan smiles a little, "Wow you are really laying on the compliments tonight. How much have you had to drink? Maybe we need to keep you away from the open bar."

"Actually, my generous mood is not alcohol induced." She seems surprised, almost as she says. "I'm just happy. And I'm happy you're here with me."

"I still don't see why you brought me and not Nate." Dan can't help saying. " Isn't he like the ideal guy to bring as your wedding date?"

"He would please my mother too much. Besides, he was in Vermont this weekend with his family. You were perfect. Look at her," She swivels around the dance floor so Dan can see her mother's dismayed expression. "She's practically fuming at my choice in date." Blair's smile is mischievous.

"How dare anyone allow someone not Upper East Side born-and-bred into such an establishment?" Dan jokes and they both laugh. "Imagine her horror if you catch the bouquet tonight."

"I won't subject myself to such an undignified display of desperation." Blair declares with a defiant lift of her chin. "Besides, I don't need any luck securing myself a husband. I could be married right now if I wanted to."

"Really?" Dan says with mock interest. "To who?"

Blair seems to contemplate this. "You."

Dan stops dancing for a second, leaving them standing still momentarily. "Me?"

Blair's face breaks into a wicked grin. "You, indeed."

"Why do you say that?" Dan remembers how to dance again and begins moving his feet again.

"The reason is twofold, one it's the perfect way to torment my mother, two it's the perfect way to torment you. Marrying you would piss off my mother far more than just bringing you as my date tonight did. As for you, we could just spend our whole lives bickering and bantering. We practically have the whole marriage thing down already, don't you think?"

Dan seems to think about this. "I guess, you're right. But seriously, if you had to marry one of the guys you know right now, who would it be? Nate?"

Blair laughs, "You're kidding, right? I love Nate, as a friend, and think he's a great guy. But he's restless and unable to keep his focus on one thing, let alone a person, for more than 10 minutes. Within a month Nate would have slept with the maid, at least one of my friends, my hair stylist, hell, probably even Dorota. Besides, like I said I would choose you."

Dan's face turns serious and all trace of joking disappears as he stops dancing and takes both of her hands in his. "Blair Waldorf, will marry me?"

For a moment, he maintains a sincere expression with no hint of mischief until finally, she catches the edge of his lips twitching.

"Dan, stop, people are turning to look at us." Blair looks worried and her eyes dart about the dance floor.

"Oh you're right, I'm not doing this correctly." He starts to lower to the ground before she discreetly kicks him and forces his hands back into the proper dancing position. She begins leading them back around the dance floor.

"There's only so far I'll push my mother. Getting engaged, even if it is fake, at my cousin's family will get me banished from this family." Blair says before breaking into laughter. "I must say though, you are rather good at acting. I may need you to repeat that ruse at some point in the future if I'm feeling really irritated with her. I almost even bought it."

Once the MC announces the dreaded bouquet toss is coming up, Blair suggests they go explore the garden that's just outside the reception hall. Dan follows her out into the brisk night and can't help but feel a bubble of happiness. Maybe he was wrong, he decides, perhaps this night wasn't a bad thing for their friendship but a good one. The whole evening has passed seamlessly and despite being surrounded by a somewhat-stuffy crowd, he's found himself more relaxed and at ease than he has been in months.

Entering the rose garden, Blair pauses in front of the fountain and seems deep in thought. Dan approaches and then stands beside her. He turns to face her, trying to read her thoughts, but her expression is unreadable.

"What are you thinking?" Dan finally asks. The only sound so far has been the water trickling into the basin of the fountain.

Blair's reverie seems to be broken as she turns to him. She smiles and then shakes her head. "Nothing, really. I just," She hesitates for a moment. "I'm really glad you came with me tonight."

Dan feels her hand brush against hers and now notices for the first time how close they are standing. He tries to ignore the spark of electricity he felt at the contact and looks away, briefly. "I'm really glad you brought me."

There it is again, he thinks, that shift he sensed earlier. They had a similar conversation on the dancefloor with Blair proclaiming her happiness at his presence here tonight but now, it's different. It's like she's trying to convey more with those words and Dan feels a rush of trepidation.

"Isn't it weird," She begins, her tone more wistful now. "To think of a year ago at the museum... That day when Nate and Serena canceled on the museum plans and were both horror-stricken to find it was just the two of us."

"I wasn't horror-stricken." Dan cuts in.

Blair tilts her head to the side, with a knowing expression. "Yes, you were. You should've seen your face. You were helplessly scanning the crowds hoping to see one of them. I honestly thought you might pretend to know a stranger you were so desperate to escape my company." She seems to survey Dan's face and then add, "It's okay. I was a bit horrified too."

Dan relents, "I guess I was a bit taken aback."

"That's an understatement." Blair gives a little laugh. "Anyways, that's my point. A year ago the idea of it being just you and I was panic inducing. But now…" She trails off and fixes her gaze on him.

"There's no one else I would rather be with." Dan says before he can stop himself. His heart pounds harder with nerves as he wonders how Blair will react. He feels her hand slowly, tentatively, start to entwine with his. As his eyes drop to her lips, there's a sudden eruption of cheers and Dan remembers where they are. The wedding. The wedding which Blair brought him to in order to… Piss of her mother. He drops her hand and clears her throat. "We should get back inside. It sounds like it's safe now, that had to have been someone catching the bouquet."

Blair takes a step back, "Right. Of course." She turns on her heel and walks briskly, leaving Dan to follow behind.

Later, when he looks back on that night, he won't be able to wonder to help but wonder what would have happened had he ignored the commotion from inside the wedding or the reasons why not. But the truth is, he knows exactly what would have happened. Even if he's too afraid to admit it.


	9. Chapter 9

**Back to the present :) Also, I'm running low on flashback ideas so if you have a suggestion or request of some sort of scene between them you'd like to see let me know! I hope to update again by Thursday. Thanks for reading!**

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The next day passes in a blur of flowers, desserts, and table settings. With it being the day before the wedding, there is a multitude of last minute details to arrange which Blair and Dan help with. They do everything from visiting the local bakery to pick up the cake order to updating the seating chart with last minute RSVPs. Then, in the late afternoon, Blair attends the wedding rehearsal while Dan stays back at the villa and swims. It's a much-needed reprieve from the seemingly endless wedding activities.

Climbing out of the pool and feeling refreshed, Dan heads to his room to get ready for the rehearsal dinner. After showering, he changes into a simple white button down dress shirt paired with a skinny tie, navy chinos, and wingtip shoes. He was instructed by Blair to dress formal yet casual but to err on the side of overdressed. She said although he had impressed her with his outfits so far on the trip, she didn't want to be proved wrong and spot him at the dinner in a flannel shirt and jeans.

Musing his hair, one last time, he turns away from the mirror and heads out the villa. When he arrives at the dinner which is held in the formal dining hall of the main house, Blair is fixing the large garland that streams across the table. Hearing him enter, she looks up and smiles.

"Hi." Her eyes drop and scan his attire. "You dressed up." Her smile widens.

"Well, I was fairly certain if I didn't you would have me escorted to the airport and sent on the next flight to JFK." Dan deadpans standing across from her.

"I don't know if my action would be that severe. But maybe."

"Where is everyone?"

"Enjoying cocktails on the terrace. I was just making sure everything looked perfect before the dinner started. We can go out and join them though. I need a drink."

Dan follows her outside and once they are at the makeshift bar, he asks what she wants to drink. "Wine? Rose?"

"Something much stronger than that." She reaches for a bottle of gin. "This will do."

Dan pours them each a drink and then Blair proceeds to fill him in on the rehearsal. "The wedding coordinator is dreadful, I'm telling you. She suggested I 'sprinkle rose petals' down the aisle. Like, hello, I am not a fucking flower girl. How old do I look to you?"

Dan laughs, "Isn't it better she thought you were young enough to do that though rather than too old?"

Blair seems to think about this. "I suppose. But still, it's a terrible idea and one she should have been fired for." She rolls her eyes. "Anyways, how was your afternoon?"

Two hours later, and 3 drinks later, they pull their chairs out from the table having just finished dinner. Blair suggested they escape for a bit before dessert is served and Dan couldn't blame her. They were seated next to Blair's aunt, Rosamund, who calling chatty, would be an understatement.

It's dusk as they exit the dining hall and the stars are beginning to emerge in the night sky. It's peaceful and serene with the only sounds being that of Blair's heels clicking on the cobblestone and the distant sound of laughter and jovial voices.

"I wanted to show you something," Blair leads Dan through a walkway which he hasn't passed through before. "I saw this today after the rehearsal. It's amazing."

After a short walk, they arrive at a vine-covered door. Blair pushes the door open to reveal a walled garden. Dan follows her in, stunned by its secrecy and beauty and she closes the door behind us.

"Isn't it amazing?" She breathes. "A secret garden…"

The expansive garden is filled with an assortment of vibrant flowers, swirling vines, and a large Tuscan fountain in the center. As Dan takes in the sight, his eyes fall upon a vision of pink blooms. "Peonies. No wonder you love it."

Blair nods and walks over to the peonies. "The most beautiful flower in the world. Whoever gardened this has good taste."

Dan strides over to the fountain and can't help noting, "This place, it sort of reminds me of that garden at your cousin's wedding venue."

He's not sure why he said it aloud and he instantly wonders if he made a mistake in bringing up the unspoken evening. But Blair's wistful voice relieves him of his anxiety.

"I thought the same thing. Maybe that's why I love it." She says, joining him by the fountain.

He can't bear to face her because he doesn't want to be betrayed by his emotions. Whenever he's thought of that night, he gets this strange longing and a sort of sadness. She's close enough that if he was to turn away from the fountain to face her, she could read each and every detail of the expression that would pass his face. So he remains silent, gaze fixed on the trickling water.

"You know, that night," Blair begins in a low voice. "I thought you were going to kiss me." She says it so quietly that Dan almost wonders if he misheard her. But as he turns to survey her expression, he knows he heard her right. Her eyes break away from his.

"I was." Dan surprises himself by admitting the truth he's withheld for two years. The relief is so palpable he doesn't regret saying it. At least, not in the moment.

Blair looks up, sharply. "You were?"

Dan can only manage a nod.

"Why didn't you then?"

Dan can't bring himself to meet her eye. "I thought you might not kiss me back. The night had been so perfect, I didn't want to ruin it." He meets her gaze.

"You're lying," Blair says in a cutting tone, narrowing her eyes. "You know I would have kissed you back. We were inches apart, I reached for your hand, it was written all over my face. You had to know."

Dan takes a deep breath and then meets her eyes. "Fine, you're right. I knew you would."

"So why didn't you?" Her expression is one of confusion and hurt.

"Because for me it would have been real and for you, it would have just been another act of rebellion to defy your family's expectations."

Blair's gaze hardens as she says, "It would have been real for me too."

Dan is unable to speak for a moment until at last, he says, "I didn't know."

"How couldn't you have? I brought you to the wedding, Dan. I only wanted you there."

"You told me it was because whatever the name of that guy you were dating at the time was couldn't go. And that Nate was away."

"I lied. I only wanted you there."

"To piss off your mother."

Blair shakes her head. "That's not why. Besides, I made it pretty clear later on that that wasn't the only reason." She looks away sadly and then turns back to face him, "You know, I convinced myself that I imagined it all. That we didn't almost kiss that night. I thought I read more into it and you hadn't been thinking the same thing I was. But now, you just proved I was right then. And that you think so little of me, you didn't even give me the chance to kiss you back." With that, Blair flees the garden.

Frozen momentarily, Dan shakes himself from his trance and runs through the hedges to catch up to her. She's already flying up the stairs back towards the rehearsal when he calls her name.

She ignores him and keeps heading up the wide set of stairs, he doubles his pace to catch up. "Blair. What the hell? Why did you run off? We need to talk about this." He can't help but sound incredulous. Less than thirty minutes ago they were laughing together and now, the turn things have taken is almost unbelievable.

She whirls around, "No we don't. There's nothing more to say." Then she picks up her pace.

Dan finally manages to catch up to her and gently grabs her arm. He looks at her pleadingly. "Will you tell me why you're upset?"

She shakes out of his grip and lets out an annoyed sigh, "Are you serious? You don't know why I'm upset? Were you not listening?"

"Why you're really upset, I mean. It still doesn't make sense." Dan wants to add, It's not too late for us, but he refrains because he has a feeling that won't go over too well.

"Two years Dan. Two fucking years were wasted because you didn't just kiss me when it was painfully obvious I wanted you to."

"So now what? We just aren't going to talk about it?"

"No, I think that ship has sailed." Blair's eyes are like lasers cutting through him. "This is what I was talking about. It's Pandora's Box, this conversation, and now irreparable damage has been done. By the way, since you have trouble reading signs, no matter how blatant they are, we're not friends anymore. I wish we weren't stuck in another fucking country together but we are. So please leave me alone so I can try to make the best of this fucked situation."

Dan scans her face and sees just how serious she is. With her icy glare and stone cold expression, he knows there's no chance he can get through to her now. With a sinking feeling, he relents. "If that's what you want then I'll get the next flight out."

For just a nanosecond, so short he would have missed it had he blinked, her expression changed to one of almost... Remorse. But within a fraction of a second, it was gone and just her hard stare remained before she turned on her heel.


	10. Chapter 10

**Thank you guys for the suggestions! I ended up combining your requests :) _J_ , I loved the Blair and Jenny idea so thank you for the input and _RF_ , I totally agreed a happy flashback was needed. So here we are! Hope you all enjoy and thank you to each and every one of you for reading and reviewing! **

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One and a Half Years Ago

Armed with a tray of four hot chocolates, Dan pushes open the door to the loft to find Blair already waiting for him. Then, he spots Jenny sitting beside her and he instantly panics. Shit, he thinks to himself, she will be extra furious with me for running late.

Ready for a glare and an icy tone, he tentatively greets her. "Hi, Blair. Sorry, the cafe was packed and I had to wait in a huge line."

She turns away from Jenny, a smile on her lips. "No worries. It looks so good." She gets up and grabs two of the cups and offers one to Jenny. "We're so excited, I haven't had hot chocolate in forever."

"Oh, you are?" Dan can't hide his surprise. Why isn't she mad, he wonders. Blair is a stickler for punctuality and almost always avoids alone time with Jenny due to their rocky past at Constance Billard. He almost asks her why she isn't yelling at him but decides asking for a lecture would just be inane.

"Of course! The best part of the Christmas season is the hot cocoa, everyone knows that. Anyways are you ready? Your dad already pulled the car around and is waiting out front for us."

"I know, I saw him on my way up. Let's go then." He says, holding the front door open for them.

Going Upstate to cut their own Christmas tree has been a Humphrey family tradition for years. Every year, Jenny, Rufus, and Dan pile into the old Bronco SUV armed with hot cocoa and Christmas tunes to play on the hour long car ride. This year, however, is the first that Blair will be joining them. The whole idea came about after Dan found out she had never cut her own Christmas tree so he suggested she join. She had been wary given it was a family thing but he insisted no one would mind and sure enough, Rufus insisted she come.

The only part of Blair joining on the holiday escapade Dan was worried about was the dynamic between her and Jenny. Though their high school days were long forgotten and both girls had outgrown petty power struggles involving cliques, there was lingering tension. Over the past two years, it had certainly diffused slightly since Dan and Blair hung out so frequently but he always made sure to never leave them in a room alone for fear of it being awkward. So when he made that error by being late today, he couldn't help but be apprehensive.

But the two continue to surprise him by chatting in the car. He can't remember ever hearing Blair and Jenny carrying on a conversation of their own. Listening, he catches on that they are talking about fashion week coming up in two months. Then, they discuss last season and which collections they loved and which they hated. Relaxing a bit in his seat, he realizes perhaps this adventure was exactly what the two needed to finally bond.

An hour later, Dan and Rufus are debating which size tree to cut. Rufus wants the 6 foot 4 tree but Dan is exasperatedly insisting upon the 6 foot 2 because he knows the other won't fit in the loft.

"Does this happen every year? I can't help but think that it would seem after years of doing this, the tree height would be predetermined." Blair's voice is faintly heard over the heated discussion.

Jenny groans and he can imagine, rolls her eyes. "Yep. It's ridiculous. Dad gets all caught up in the Christmas spirit and forgets how low the loft ceilings are, insists on the tallest tree, then has to cut it down when we get home because it doesn't fit."

Blair laughs, "For how long will Dan keep trying to talk him out of it?"

"However long it takes." Dan cuts in.

Jenny shakes her head. "We could be here for hours." Then an idea seems to strike her. "Hey the shop up front is pretty cute. We could go look at decorations and wreaths while they battle it out."

"Yes, please." Blair says and Dan watches in astonishment as her beret-clad head follow Jenny towards the shop. It truly seems that this normally fruitless fight between himself and his dad will finally result in some good. He smiles as the two walk side by side, chatting like old friends.

The next day, the loft is empty save for the reunited group of best friends; Nate, Serena, Blair, and Dan. Under the 6 foot 3 Christmas tree, a compromise between Dan and Rufus, sit an array of glimmering packages wrapped in bows. Blair suggested they do their annual gift exchange at the loft this year since it was bound to be the most festive location given the tree and decor purchased yesterday.

"Okay, Dan you haven't opened any yet." Serena says as she reaches under the tree. "Here, open this one from Blair."

Dan takes the neatly wrapped silver package which is adorned with an expertly tied ribbon. He imagines Dorota must wrap all of Blair's gifts unless she's secretly been trained at Santa's workshop. He gingerly unwraps it and at last reveals an antique looking book. He looks to Blair who looks nervous, almost, as though she's waiting to see his reaction. He flips it over to see the title. On The Road by Jack Kerouac, one of his favorites.

"It's a first edition signed by the author." Blair says as he scans the title. "Open it."

Dan opens the cover to reveal a scribbled signature on the front page.

"Do you like it?" Blair says, tentatively. Dan thinks that must be the first time she's ever asked anyone that question. Blair is usually more likely to convince someone they like something rather than to question it.

"Blair, this is amazing." Dan says in admiration. "Where did you even get this?"

"Oh, it was nothing." She says with a smile. "I'm glad you like it."

"Of course, I love it." Dan hesitates but then proceeds to walk over to her and embrace her. "Thank you." He says into her hair, smelling the faint scent of vanilla bean. Pulling away, he heads over to the tree to retrieve her gift.

"Nice job, B." He hears Serena say to Blair as he pulls out the gift.

"So my gift is nowhere near as impressive as yours, I must warn." Dan says as she begins sliding the paper off.

From it, slides out a 20x28 portrait of Audrey Hepburn matted and framed. In it, she wears a tassel adorned hat which was designed by Givenchy. Blair flips it over and then gasps. "Dan, no way. Please tell me this isn't the one from the auction."

"It is." Dan admits sheepishly.

Her doe eyes widen, "Dan, what? How?"

"I bid on it when you weren't looking and I won." Dan shrugs nonchalantly. Dan had indeed knew he would bid on the portrait as soon as Blair pointed it out. It was the same auction they had nearly two years before, this time without Serena and Nate. Blair had joked that if Nate and Serena were here she would be called out for being a hypocrite for being just as predictable as they were. But still, she stared longingly at the black and white photo. When she went to the restroom, Dan bid after doing intense research online on how much exactly one should bid at a silent auction. Luckily, the winners were informed privately so she never even knew until now.

"Oh my god. I can't believe I now own an original photo of Audrey. You really really shouldn't have though."

Serena who previously looked too shellshocked to speak finally says something. "Dan, how the hell did you even afford that? Doesn't that cost like what a lifetime's work of published, paid work as a writer?"

"No, it wasn't that much." Dan says, embarrassed. But she's not far off. He paid for it on a credit card which he imagines he won't be able to pay off until he's 50. But just one glance on the still amazed expression on Blair's face and he's reassured that it was worth it.

Blair comes over and gives him the tightest and warmest embrace he has ever experienced. As a somewhat prickly person, Blair isn't one to hug often, even Dan knows that. But her making an exception for him brings an even happier glow to Dan.

"Well, fuck. None of my gift's for you guys are half as good as that." Nate says once they've pulled apart. "Can we postpone the rest of the gift exchange until I've had time to exchange these for something better?"

"I second that!" Serena says. "You guys really showed us up. You could've warned me, both of you."

Dan laughs, "No whatever you got will be fine. It'll be better than fine, I'm sure it's great."

Blair agrees, "S, come on. You always get me something I love. I'm sure this year won't be any different."

"Alright, but don't say I didn't warn you," Serena says in a teasing voice as she hands over a candy cane printed gift bag to Blair.

"Let's face it, Serena. We won't be invited back for next year." Nate jokes before the group resumes their gift exchange.

Dan smiles at Blair one last time, before turning his attention to Serena opening her present from Blair.


	11. Chapter 11

**Okay, so originally I was planning on this chapter having some answers but after reading all your comments, it seems like you guys like the group dynamic between Dan, Blair, Nate, and Serena. So I decided to extend some scenes which I hope you all will like. Answers will come in the next present tense chapter. Thanks so much for reading!**

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As Dan is wheeling his suitcase into the living room, Blair walks in still sporting a glare. But Dan hears what sounds like more footsteps and voices rapidly approaching their door.

"Look who I found." Blair says in faux enthusiasm, her face appearing to smile but coming out more as a grimace.

Suddenly, Serena bursts through the door and throws her arms around Dan. "Did you miss me?" She steps back to survey him and frowns momentarily. "You should look happier to see me but I'll take it as just shock for now."

"Serena…" Dan says and then spots someone else behind her. "Nate?"

"Hey man," Nate comes forward and they clap each other on the back.

Dan is in such shock, he can hardly react. He looks to Blair who looks equally stunned. Serena seems to notice the suitcase now and furrows her brow. "Aw, you knew I was coming! Blair, I told you not to tip him off, did you text him as we walked over? That's so sweet of you to clear your room for me, Dan, but it's really not necessary. I'll stay in Blair's room and Nate can take the couch. Right?"

"Works for me," Nate says and Blair nods in accordance, sealing the plan.

"Nate and I need to go grab our bags from the cab. We'll be right back!" Serena beams at them before the two of them exit the room.

As soon as they're gone, Blair shuts the door. "Obviously you aren't leaving now and neither of us will be breathing a word to them about… what happened." Her expression is so cold and her tone so icy that Dan can only manage an automatic nod. She looks to his suitcase, "Put that back in your room. You're lucky Serena assumed it was it was for her, classic." She rolls her eyes momentarily and then seems to remember she's mad at him so her face turns to stone again. "The last thing I would need is you abruptly leaving and me having to explain why to them."

"So are we going to talk about it?" Dan asks, hesitantly.

"No, we aren't going to fucking talk about it. Were you even listening?" She shoves his suitcase at them. "Put that away!" She exhales loudly, seemingly releasing some of her anger and then composes herself. She walks over to the door and reopens it just as Serena and Nate approach.

"I'm so glad you both are here! It's the best surprise!" Blair says happily, surprisingly convincingly given her rage just a second ago.

Once Nate and Serena are unpacked, they all reconvene in the living room. Blair immediately heads to the kitchen to pour everyone drinks. She downs hers immediately and refills it before rejoining them. She makes a pointed effort to sit as far away from Dan as possible by sitting on the outermost edge of the couch she shares with Serena. Meanwhile, Dan and Nate occupy chairs across from the couch with Dan diagonal from Blair.

"So tell us, what have you two been doing? We're sorry we couldn't join sooner!" Serena says with a bright smile as they settle.

"It's been uneventful," Blair says quickly. "I want to hear about you guys. How did you end up here together?" Her face creases in brief agony. "It was so unexpected. Wonderful though, of course."

"Do you want to tell them or should I, Natie?" Serena questions Nate.

"Go ahead Serena, you'll probably make it sound far more exciting than I could." Nate says with an encouraging nod.

Serena seems relieved and bursts out with the story. "So I was in Monaco meeting up with some friends I met at Fashion Week, you know during my brief modeling stint." She says breezily. "Then one night, we're at the bars drinking and of course nearly everyone is speaking French. But then I hear this American and I spot an oh-so-familiar site of tousled brown hair with golden streaks. I'm thinking, 'Oh my God, this guy looks just like Nate.' So obviously I have to introduce myself and maybe even show him a photo of his New York doppelganger. As soon as he turns around, I nearly drop my drink. It was Nate! Can you believe it? Both of us just so happen to be at the same bar in Monaco at the same time."

Dan takes a sip of his drink, feeling as though he's enduring something. This story is seemingly going to go on all night. Taking another swig, he tunes back in.

"I mean, we both were so shocked. It had turned out that Nate had sailed into Cannes and then traveled up to Monaco. We spent the week together and then headed here!" She lets out a breath as she finally concludes the story.

"Wow," Blair says and Dan notices she looks just as weary as he does. "Amazing."

"The four of us reunited at last…" Serena says dreamily. "It's like it was fated."

Dan thinks he hears Blair mutter something under her breath but can't quite make it out.

For another hour or so, they hear more of Serena and Nate's travels. Around 11, Blair finally says she's tired which concludes the gathering. Heading to his room, Dan feels a swell of relief at finally being able to be alone with his jumbled thoughts and emotions.

The next morning, Dan enters the living room to discover a huge breakfast spread adorning the dining room table. There's slices of bread, jams, fruits, and cheeses on an array of platters. Then, he sees several pitchers of mimosas, one of which is already nearly empty. He glances at the clock on the stove to see it's already 9.

"You're finally up! I was about to come in and jump on the bed to wake you up!" Serena says as she comes in from outside with wet hair, wrapped in a towel.

"Good morning," Dan says, still a little bleary eyed. "What's with the feast?"

"We ordered room service. When in Tuscany…" She says airily. "We helped ourselves to mimosas already but he waited for you to start eating." She turns back towards the glass doors which lead outside. "Nate, Blair! Dan is finally up so let's eat."

Dan pulls out a chair as Nate and Blair come in from outside. It looks like Nate went swimming too judging by the pool of water that forms around his feet as his strands of hair drip water. Blair, on the other hand, seems dry and is wearing a sun dress and lace-up sandals. He pulls out the chair beside him for her but she ignores him and sits next to Serena instead. Luckily, no one else seems to notice the snub.

"What's the plan for today?" Nate asks, grabbing a slice of bread.

"Well, the wedding isn't until 6…" Blair says as she sips a mimosa. She tries to reach for the bowl of fruit but can't so Dan pushes it towards her. She reluctantly takes it but doesn't meet his eye or acknowledge him.

"I would ask you two what you think we should do,:" Serena gestures at Dan and Blair. "But I know what you'll suggest. Something boring like a museum so I think Nate and I should choose. What do you think Nate?"

Nate shrugs, "I'm good with anything."

"How about we rent Vespas and ride around the countryside. Maybe go to a winery or two?"

"I'm all for that minus the Vespa thing. Let's just order a car."

"That's no fun, Vespas! Vespas!" Serena begins chanting.

"I don't know how to ride one," Blair whines.

"But isn't that like your lifelong dream? It'll be just like Roman Holiday. I call Nate though so you can share one with Dan."

Blair chokes on her mimosa and begins fervently shaking her head. "Have you seen Dan drive? He drove his dad's Bronco on the way home from the Christmas tree farm last year and almost killed us all by swerving suddenly."

Dan glares at her. "That's a complete exaggeration. Furthermore, I was trying to avoid hitting the deer. "

"True but you didn't have to swerve so jerkily, I had whiplash for days afterward."

"Really, why don't you drive then next year?" Dan narrows his eyes at her.

"Like they'll be a next year." Blair says with hostility.

"Woah, I didn't realize this was such a sensitive topic." Serena cuts into their bicker. She's apparently convinced this is all due to the Vespa debate and seems unaware of the deeper conflict. "Okay, no Vespas then. Or Blair rides with Nate."

"I will happily ride with Nate," Blair says with a pointed look.

"Actually, I have some work to do." Dan says suddenly, unable to take the tension anymore. "Why don't you three go on without me?"

"No way!" Serena cries, shaking her head vehemently.

"Really, I don't mind. I'd just rather stay back and get some stuff done."

Blair finally looks at him, her expression softening and he sees the effort it takes for her to manage an even tone. "Dan, come on. Serena's right, you have to come. You can't be in Tuscany and spend the day working."

Dan still shakes his head and begins clearing his breakfast plate, leaving the three at the table. A moment later Blair comes into the kitchen, Dan ignores her as he scrubs the plate.

"Dan," She begins. "Look, I'm sorry, okay? I know things are…" She breaks off, sighing.

Dan swivels around, reluctantly, to face her. He sees she truly looks remorseful.

"Anyways, the point is. Even if we are fighting or not friends or whatever, you should still come. I'll try my best to get along." She gives him a tentative smile.

"I don't know…" Dan says, wiping his hands on a dish towel and then placing them in his pockets. "I just think it would be easier if we spent some time apart, with everything that's happened. Besides, I know you're just worried about what Nate and Serena will think."

"It might be easier but it wouldn't be the same. And I don't care I mean obviously I'd rather not give them the run through…" A flush is rising to her cheeks. "But it's not about that. It's just that the four of us haven't all hung out together for so long." She adds as an afterthought. "I'll even ride on the Vespa with you."

Dan can't help but give a small yet brittle laugh. "That's really not necessary. His resolve breaks at the sight of her sorrowful expression. "I'll go."

Blair sticks her hand out, "A 24-hour ceasefire?"

"Deal." Dan says shaking her hand. He holds on for a second too long before remembering what hand holding brought upon them the last time and drops her palm.

Despite her initial enthusiasm about the idea, Serena eventually backs out of the Vespa plan. Blair points out that if they ride Vespas they'll have to gauge how much they're drinking otherwise they'll all end up injured before the wedding. The four order a car and pile in the extra roomy town car a couple of hours later.

While things are still far from the norm with Blair, a bit of the friction between them has thankfully dissolved due to their chat this morning. She ends up sitting next to him in the car after visiting the first winery and doesn't complain once.

By the second winery, the buzz supplied from all the wine tasting seems to have further evaporated the hostility of last night. This time when climbing back into the car, she gestures for him to sit next to her. With the way the four chat and reminisce on old times, Dan momentarily forgets all about the uncertainty of he and Blair's friendship. He only remembers when Serena brings up a time when they were also faced in a precarious situation.

"Okay so we have to admit something to you guys." Serena says as the car whirls around the windy back roads of the countryside. She looks to Nate who looks a bit uncertain of what she's about to say. "So, when I left New York, after Nate, he and I made a bet." Nate and Serena both sport sheepish expressions.

Dan looks over to Blair who's face is creased with apprehension. "What sort of bet?" She asks steadily.

"Well, we bet that you two wouldn't last as friends once we left."

"Ah, the glue theory." Dan says.

"Oh right," Blair says in remembrance. "You both thought you were the glue holding together all the friendships."

"Not thought, knew." Serena corrects. "Anyways, obviously we were wrong so I thought I would fess up after all this time." She smiles, cheerfully. "I mean, you two are closer than I would ever thought possible. I remember the first time you two hung out alone, by accident, of course. Blair, I had never heard you so... What word is stronger than furious?"

"Apoplectic?" Dan offers.

"That's about right. She was furious at me ditching you guys." She turns to Nate. "Somehow it didn't seem you got any of the wrath for bailing."

Blair cuts in "I was not apoplectic. That's an overstatement. I was merely disappointed in your flakiness." She says haughtily.

Nate laughs, "I remember that, even if I wasn't the one receiving the brunt of it. Serena was worried you'd never speak to her again."

"No, not true." Blair says defensively.

"It's okay, Blair. It's fine if you weren't too thrilled about being alone with me that day. It's not like it wasn't clear from the way your eyes darted about, looking for an escape route." Dan tries to sound more nonchalant than he feels.

Blair frowns. "Now I feel bad."

"Don't, B!" Serena says. "My point is, look how it turned out. I'd put my money these days on you two outlasting any other friendship I know." At her words, the sharp pang of sadness hits Dan. If only she knew…

He glances to Blair to see if she's feeling the same way but her expression is impassive so he tries for a carefree tone as he asks, "Out of curiosity. How long did each of you wager?"

"4 months." Serena says. "Nate was rather generous though, weren't you? Tell them…"

Nate shrugs. "I always thought you two got along well so I said two years minimum or until one of you got married if that happened first."

"I agreed with that." Serena nods emphatically. "You know, I'm sure a spouse wouldn't want their betrothed that close to someone of the opposite sex. For obvious reasons." Serena adds as an afterthought.

 _For obvious reasons?_ Dan thinks to himself. What the hell? It's as though she's deliberately hinting at something. He decides he's overthinking this though and brushes it off.

"Anyways the bets are off now." Serena says.

From the way in which neither of them react, Dan knows that he's the only one to hear Blair say, quietly, "I wouldn't be so sure."


	12. Chapter 12

**I have a new Dair story idea which I started writing an outline for. But I have a question for the new story, it will need a secondary love interest for Blair** **. So I need to know... Do you guys want it to be Chuck or Carter or an original character? Any of those options will work so I thought I would leave it up to you guys :) Thanks in advance! P.S.** **It's safe to say I'll have at least two more Dair stories (if not more) in the works since I also still want to write the camping story. I'll basically keep writing for them until you guys get tired of reading or I run out of ideas which hopefully won't be for a while.**

 **As for this chapter, this flashback is inspired by episodes 4x15 and 5x02. Hope you enjoy!**

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One and a Half Years Ago

Blair sets down her now empty gin and tonic with a thud on Dan's counter. "I just can't believe I got dumped let alone two days before Valentine's Day. I knew I should have fucking dumped him first." She shakes her head. "Note to self, always break-up with the guy before he can break up with you."

"He's an idiot," Dan says, vehemently as he refills her glass. "It's his loss."

"Of course it is." She sighs. "Anyways, you're single too so I was thinking let's not be lonely losers and let's have an anti-Valentine's Day together."

"You want to spend Valentine's Day together?" Dan asks, making sure he heard her correctly.

"Anti-Valentine's Day. Nothing remotely romantic, nothing red or pink, no candy in the shape of hearts. Instead," Blair puts a finger to her chin as she thinks. "Maybe a horror movie, tequila, basically anything and everything unromantic. We can start by watching Who's Afraid of Virgina Woolf? Oh and Gone Girl is a must." She turns to face him. "You in?"

"Sure, my place or yours?"

"Yours. I'll bring the alcohol. Also, I had another idea, let's make the movie marathon a drinking game."

Dan laughs, "How are we going to do that?"

"I'll make up one." She starts rattling off ideas, "Drink whenever there's blood, drink when someone suspicious turns out to be a red herring, and then, of course, finish your drink when someone is murdered. That sort of thing."

"It sounds like we could end up pretty wasted." Dan says, wincing.

"That's point." She smiles brightly. "I got to go get started on all of this, see you Friday!"

Dan spreads out all the movies Blair requested across the table, waiting for her arrival. Yesterday, per her instructions, he went to rent them from the rental place down the street since only one of the suggested movies was on Netflix watch instantly. So now, his coffee table was covered in very unromantic movies. He arranges them in order of watching, Gone Girl, Who's Afraid of Virginia Woolf?, Rosemary's Baby, and The Shining.

Just as he steps away from the table to go make the popcorn, Blair walks in, armed with a massive bottle of tequila. "Hey," She's wearing what's supposed to be a very un-Valentine's Day outfit Dan notices. But he still can't help but think how beautiful and very Audrey-like she looks in her black skinny jeans, black cashmere sweater, and beige ballet flats which she kicks off by the door.

"Hi," His eyes drop to the bottle. "How much are we planning on drinking?"

She seems to think about this. "Who knows, maybe the whole thing." She puts it down on the table and heads into the kitchen to get glasses. "I brought lemonade we can mix it with. I was originally intending for us to do shots but decided that might be lethal by the third movie."

Dan nods, "Probably best we make very diluted drinks with it."

Blair tilts her head, "You're kidding, right? They will be the opposite of diluted." Proving her point, she pours two shots into each glass and then only about 8 ounces of lemonade. She hands him his glass and then heads to the couch, making herself comfortable.

As the popcorn finishes popping, Dan puts in her first choice, Gone Girl. Meanwhile, Blair seems to be digging for something and moments later pulls out a blue notecard covered in her neat handwriting.

"Okay, here's the drinking game I made. It's pretty clever if I do say so myself." She sets it on the table and Dan picks it up.

His eyes widen as he reads through it, "I'm not sure I'll survive this."

Blair laughs as he settles down next to her and the movie begins.

Dan gets up to put in Rosemary's Baby and finds he's much drunker than he realized. He accidentally trips over his laptop charger which ran across the living room, sending Blair into a fit of giggles. Once the movie is in, he turns back to survey her. "Admit it, you are drunk. Drunk enough that we can end this ridiculous drinking game."

"No way, it's too fun. You wince every time you take a sip."

"Yeah because you've been increasing the amount of shots so much in each glass that it's about 90 percent tequila and only 10 percent lemonade." He sits back down next to her, scooting closer so he can share the blanket that's draped over her. Their hands brush as he spreads it out over them. "Anyways, who said in order to have a successful anti-Valentine's Day you have to be wasted?"

"I did. So that makes it the law." She says very dramatically, dragging out each syllable. Suddenly, she yanks the blanket. "Stop stealing this! You have more of it than I do and I'm cold."

"No," Dan says, tugging it back over him. "It was perfectly even. You're the blanket thief."

"Am not." She says, crossing her arms over her chest. She imitates a shiver. "So cold. What kind of friend are you? You're just going to let me freeze?"

Dan lets out a frustrated breath and then adjusts the blanket. "See it's perfectly even." He gestures.

"Still too cold." She suddenly scoots so there's no more gap between them and then tugs the blanket up to her neck, still leaving both of their legs covered. "Much better." She sighs happily.

Dan contemplates pointing out that certainly sitting this close to someone especially a fellow single person on Valentine's Day doesn't seem unromantic but decides against it. Her warmth against him is so comforting that he can't help but settle into the new seating arrangement as he presses play on the movie, silencing their blanket debate.

They only end up making it halfway through the movie, Blair falling asleep on Dan's shoulder by the midpoint. Feeling exhausted himself, but too comfortable to wake her he decides maybe they can just take a nap. He will rest his eyes, just for a little while, he tells himself. It's not until morning though that he wakes up again, Blair still sound asleep beside him.


	13. Chapter 13

**I didn't want to make you all wait any longer through transition scenes so I am starting this chapter at the wedding. Hope you enjoy! Next chapter will be up on Thursday. Thank you also for the feedback on my new story. It seems like there's a mix between who everyone wants so I'm writing out more of the story to see which character will fit best. Thanks again:)**

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The rest of the day whirls by as they rush back to the villa to get ready for the wedding and then find themselves sitting in the peaceful garden ceremony. It's not until they are seated around their table in the reception hall that Dan can finally relax again. While the ceasefire helped things a bit, it mostly acted as a band-aid to still sore wound of yesterday. But now, as Blair waits in the wings of the reception hall, far from Dan, he finds the lack of tension refreshing. He knows he has to clear things up, once and for all, tonight.

The room goes silent as the melodic sound of music fills the room. The father-daughter dance is set to an Italian song and Harold leads Blair to the middle of the room. She wears a gown that Serena described as angelic. The dress has short sleeves that cap at Blair's shoulders and the neckline forms a heart on her chest, highlighting her defined collarbone. The floaty gown is swathed in pale blue feathers that complement Blair's porcelain skin. Dan's eyes stay fixed on Blair as she is spun about, gracefully. He's so lost in his thoughts, it's not until Serena's voice breaks his thoughts that he's aware again of his surroundings.

"Oh my god," Serena says in a surprised voice, keeping her voice low. Dan breaks his eyes away and turns to see what she's gasping at. To his surprise, she's staring right back at him.

"What?" Dan says, feeling self-conscious. He reaches for his water.

"That's what happened between you two. I knew something was off." Serena looks deeply satisfied. "You're in love with Blair." She says it as though it's a proven fact.

Dan chokes on his water. His coughing elicits a glare from Blair who's still dancing but currently facing him. He tries to cover his cough with his napkin. Once he regains himself, he says "Why would you think that?"

"It's blatantly obvious. You're gazing at her all love struck. Unless you're looking at Harold Waldorf which I doubt. I don't think he's your type."

"I'm not gazing at her." Dan says in an undertone.

"You were." Serena counters. "There's no use denying it. I saw and I can't unsee that expression. And to be honest, I always sort of wondered if there was something more between you two. It totally makes sense now. Does she know you're in love with her?"

"No, furthermore I'm not necessarily in love with her." Dan clarifies.

Serena seems to contemplate this. "I think you're either in love with someone or you're not. I don't think there's an in between."

"It doesn't matter either way."

"Why not? You might as well tell me. Otherwise, I'll just get it out of Blair."

Dan sighs. "Fine. I don't know where to begin. I guess it all started to unravel when my dad suggested there was something more between us." Dan continues. He tells the whole story, from start to finish, ending with what happened in the garden last night.

"Why didn't you just kiss her last night?" Serena looks confused.

"Because she said, and I quote, 'That ship has sailed.'"

"Well, why didn't you kiss her the first time? At the wedding?"

"I told you, she would have only been kissing me as an act of rebellion. She told me herself that she brought me to the wedding to anger her mom.."

Serena laughs. "You didn't seriously believe that do you?"

"Of course I did." Dan says with a frown. "That was why she chose me as her date."

"Dan, I can think of more than a handful of other guys far more scandalous than you that she could have brought."

"Maybe but she also said the other reason was that Nate wasn't available," Dan adds.

Serena rolls her eyes and then turns to Nate, "Has Blair ever asked you to go to a wedding with her? Besides this one?"

Nate looks a bit confused by the question, "No, why?'

Serena just smiles, "No reason. Just talking about weddings."

Nate seems satisfied with her answer and returns to watching the dance.

"See, I told you." Serena sighs. "You really can be quite oblivious Dan. She obviously wanted you and only you there. You definitely should have kissed her. I see why she would be mad." Serena nods.

Dan groans. "So I really fucked up?"

Serena nods, "Sadly yes. It's not like it's irreparable though. In case you haven't noticed, you two are at a wedding again. It's like you've been handed a do over."

The song ends then and after kissing her dad on the cheek, Blair makes her way over to their table. Before she's within earshot Serena says, "Seriously, don't miss your chance again."

An hour later Dan finally sees an opportunity to talk to Blair alone and decides to seize it. She's standing by the bar and waiting for the bartender to refill her glass of wine when Dan approaches slowly.

"Hi." He says hesitantly.

She doesn't turn around, her eyes remain fixed on the glass. Once it's filled, she takes it and Dan can tell she's about to walk away. "Can we go somewhere and talk?"

"Not a good time." Blair gestures to the reception which is in full swing.

"Five minutes, that's all. I just really need to speak to you." He says in a low voice.

She sets her glass on the table and then finally, turns to face him, weary. "Fine, five minutes. If only to reiterate what I thought I made perfectly clear last night."

She marches out of the reception and Dan strides quickly to try to keep up. There's guests though all around and clearly not a private spot to talk alone. Blair looks even more frustrated as she scans the vast open area filled with wedding guests getting fresh air.

Dan takes this as an opportunity, "Follow me."

She exhales reluctantly but follows him anyway as Dan can hear her footsteps behind him. Once she realizes where he's led her she glares, "Oh great idea. Let's return to the scene of the crime."

"Don't be dramatic Blair." Dan says as he opens the door to the walled garden. She's looking at him witheringly and her anger is palpable. But he doesn't let her speak first. "Let me explain. If you still don't want to be friends then fine. But at least give me a chance to explain."

She doesn't say anything and instead just looks away.

Dan takes this as his cue to continue. "But first, I need to know why you're so mad at me. You still haven't given me a real reason. I can see how I missed my chance with you, twice I suppose, but I don't see why you don't even want to be my friend."

She whirls her gaze back at him, seethingly. "You don't? Are you that oblivious? Dan, I wasted two fucking years being your friend after that night. Why would I want to waste anymore?"

He doesn't let her faze him and presses on. "Why is it a waste?"

"Because it was a waste, just being friends when…" She trails off. "I'm not getting into it. It doesn't matter anyways now."

"It does to me." Dan takes a small step forward, tentatively. "These past two years, they haven't been a waste to me. How could anytime spent with you be a waste?"

Blair averts her gaze as he comes even closer.

"That day," Dan continues. "When I asked you if you had ever thought about us… being something more, I said I hadn't. But I lied. Since the wedding two years ago, I had thought about it more than I could admit."

"Why did you lie?" Blair finally looks at him.

"I don't know." Dan runs a hand through his hair. "You had said all that stuff about how it wouldn't work, it psyched me out I guess. I wanted to tell you then though and so many other times. Now that I've been honest with you, will you just be honest with me?"

She holds his gaze and gives an almost imperceptible nod.

"Have you ever thought it?" He asks, taking another step toward her. So close now he would only have to stretch his hand out an inch or so to reach hers.

She's quiet for so long he thinks that she's not going to answer. Until at last, in a voice so low it's almost inaudible she says, "Of course I have."

At her words, Dan finally does what he should have done years ago. As he closes the remaining distance between them, he feels her arms loop around his neck. His hands come up to the sides of her face as his lips meet hers at last. The kiss is hesitant at first, as though both of them are still fearful of one another and they power they hold over each other hearts. But then, everything around them fades away; the trickle of the water fountain, the chatter of the wedding guests, the distant music. It's then that Dan gives in fully and kisses Blair with the longing he's felt for the three years that have spanned their friendship.


	14. Chapter 14

**Another Waffle Sunday flashback! The next chapter update will be this weekend. Also, in case you missed it, I've shared the first two chapters of my new Dair story A Bittersweet Retreat. Thank you to those who read and reviewed it already! :)**

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One Year Ago

As Blair reached for the maple syrup, Dan decides to broach the topic he had been avoiding. He reasoned, with Rufus and Jenny both there, maybe she would be more receptive.

"So I was thinking maybe Autumn could come over on Friday to watch Chef's Table with us." He tries to sound nonchalant but detects a trace of trepidation in his own voice.

Blair's eyes narrow at the mention of Autumn's name and she instantly pauses, mid-pour. "You're not serious, right?"

"Why not? I think it'll be fun."

"You want Autumn to watch Chef's Table with us. Autumn? Who only eats locally grown and in-season food. Who says to begin each meal with a conscious mind to promote mindful eating? Who once told me that I cut my food up in a rather aggressive manner which suggests a negative relationship with food?" Blair shakes her head and resumes pouring the maple syrup over her waffles.

Dan turns to survey his dad and Jenny, they both are watching with keen amusement. When he meets his dad's eye, he shrugs. "I mean, Blair does have a point. Autumn is rather…" He searches for a word. "Supercilious."

"Thank you!" Blair says loudly and nods in agreement. "Supercilious describes her to a T. I'm sure she will spend the whole time criticizing everything from how they eat the food to how they get to the restaurant to eat the food. She'll be saying, 'If they would have taken public transportation they could have saved the equivalent of 25 trees in the rainforest." Blair rolls her eyes. "I'm all for doing our parts for the planet, but do we have to be so judgy about it? Like I get it Autumn, you recycle and wear bamboo clothing, doesn't mean I have to."

Dan tries again, "What if she doesn't say anything at all? I'll just tell her in advance you take the show seriously."

"Dan, that show is our thing. Why bring her?" Blair gives him a look.

"Because I want you two to get along. I thought that would be a good opportunity." Dan placates.

"She's your girlfriend Dan, not mine, I don't have to like her." Blair starts cutting up her waffle and Dan can't help but agree she does sometimes prepare her food in an aggressive manner. But he's pretty sure the aggression is not towards the food itself but him. "Besides, didn't we agree to keep our relationships separate from our friendships after the double date fiasco of 2015?"

Dan winces, remembering that uncomfortable night. Somehow, it had gotten suggested that Blair and Graham, her boyfriend at the time, and Dan and Piper, his girlfriend at the time, should all go to the outdoor showing of The Sound of Music. They started the night with dinner which made it apparent that the combined group had nothing in common.

The group struggled over topics until at last, Piper found something she could chime in on. Graham's ideas about marketing, given he was in brand management. Piper then launched into how she believes multilevel marketing is the most successful tactic and then Graham said that multilevel marketing was just a disguise for a pyramid scheme. Thus, Blair's nickname for her of Pyramid Piper was born. They hadn't even made it to the movie, if Dan remembered right Blair feigned a headache.

Dan lets out a heavy sigh, "Fine, you're right. Maybe it is best to keep things separate."

"Great," Blair smiles. "Glad we are in accordance. Now, I can get the finest, most expensive cheese and wine for us to eat while watching without being guilt tripped."

Dan glances Rufus who still had a twinkle in his eye from observing the two.

Blair gets up, excusing herself to use the restroom. As soon as she's out of earshot, Rufus asks, "Why is it so important to you for Blair to get along with Autumn?"

Dan shrugs. "Isn't that normal? Everyone should want their friends and significant other to get along."

"Yeah but if it doesn't happen, it just doesn't happen. Believe me son, don't push this. Besides, maybe Autumn just isn't the girl." Rufus shrugs.

"You don't like Autumn?"

"I'm not saying that, I'm just saying… sometimes there's a reason things are easy with one person and more difficult with someone else."

Dan let out a frustrated breath, irritated with his dad speaking so cryptically.

Rufus' final remark puzzles Dan even more, "You know, when you first started hanging out with Blair, Jenny and I truly thought you had lost it. But it's been good having her around these past couple of years, I'm glad you found such a good friend." The way he says friend is strained, as though he feels the word doesn't quite fit.

"Thanks," Dan says, shaking his head at the very strangeness of the conversation.


	15. Chapter 15

**Apologies for the delay, I hate keeping you all waiting. Took me a while to find time to write this but wanted to make sure it was perfect and not rushed. Thank you all for being patient and continuing to read! More notes at the end! :)**

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"We should probably get back," Blair says, pulling away at last. She entwines her hand in his, though, and keeps her head close. "I really can't miss my own dad's wedding reception. Even if I would rather be out here with you."

Dan nods and follows her back into the reception hall. He waits for her to drop his hand before they enter but she doesn't, surprisingly. In fact, she doesn't show any hesitancy and proceeds to keep close even as they rejoin Nate and Serena. Serena's eyes immediately fall upon their locked hands and she looks up and smiles at Dan. She gives him a nod of approval before turning back to watch the dancing.

The rest of the night, Dan spends with Blair. They dance, they sit and talk properly since what feels like forever, and hang out with Nate and Serena. Even while in the moment, Dan wills the moment to lock in place in his memory. For he knows that it's the happiest he's felt in a long time. For that night, there's no analyzing what they are or what this means. That can all wait until they're back in New York.

It's not until the wedding reception has ended that Dan remembers they are currently sharing the villa with Nate and Serena. The whole night he had felt so pleased by the reunion they shared but now he couldn't help but see their presence as a deterrence. He glances to Blair as they walk back to the villa and tries to read her thoughts, unable to tell if she's thinking the same thing.

They find themselves alone when Nate goes into the bathroom to brush his teeth and Serena, having drunk too much champagne, flops down on Blair's bed. Blair closes the door behind a sleeping Serena and walks slowly to Dan. Even with the slight shadows of sleepiness shading her face, Dan can't help but be transfixed by her beauty.

"So…" Blair says slowly, entwining her hand with his.

"So…" Dan echoes, stepping closer to her. "I guess this is goodnight then."

Dan watches as Blair glances back at the closed bedroom door where Serena lies. Even he knows that as easily they could slip away into his room, it would hardly be romantic with Nate and Serena just a few feet away. Blair returns her gaze to his and nods, "I guess so. Goodnight."

Dan leans in and kisses her, perhaps a little longer than a goodnight kiss should warrant. Grudgingly, he pulls away as he hears the bathroom door open. "Goodnight, Blair."

Packing, packing, and more packing is how the four of them spend the next morning. At the harsh light of day, Dan almost wonders if last night was a dream but the look he exchanges with Blair in the morning, reminds him it wasn't. There's so much intimacy yet hesitation in that one look that it makes his heartbeat speed up. He's glad for the preoccupation of packing so he can't dwell on it too much.

He's not alone with Blair again until they're in their airport terminal awaiting their flight to JFK. They shared the town car ride to the airport with Nate and Serena since they both had flights to catch as well. Serena was off to Barcelona while Nate was going to Portugal. Dan found it curious that the two were once again off to relatively close locations but didn't press for details.

"Excited to get back home?" Dan asks Blair as he settles into the chair next to her in the terminal.

Blair takes a moment to respond, she's staring out the terminal window with a look of reverie. "I guess so." The expression washes away as her face transforms into a smile. "Actually, yes I am. I can't wait to be back in the land of the three Bs: Bergdorf's, Bloomingdales-

"And Barneys." Dan finishes for her. "I can't wait to get back and eat waffles."

Blair laughs, "You miss one Waffle Sunday and you're already desperate to have them again? Da, you are totally turning into your dad."

"I'm not that bad about the waffles. Besides, you can't tell me you honestly didn't miss them this weekend."

Blair relents, "Fine, a bit. But more so for the sake of tradition."

The two fill the time waiting for flight boarding discussing what they missed most. As good as it is to laugh with Blair and relate over the things they missed in the week they were gone, he can't help but want to talk about the subject that matters most. The one they are both clearly dodging.

The conversation fades away but Dan keeps his eyes locked on Blair's. She looks away and he steels himself to just do it. To just ask the question he's been wanting to ask for the past 12 hours. Dan waits for her eyes to meet his again, and when they do, he releases the breath he didn't realize he was holding.

"When we get back, will we-" He starts to say.

Blair cuts him off, "Let's not talk about that right now." She turns her gaze back to the window.

That's that, Dan supposes. He didn't even get the rest of the sentence out. The unasked question hangs in the air for the rest of the day and all during the flight. Blair doesn't speak to him once, except to give one-word responses to his questions such as, is this our baggage claim carousel? Or is your driver on his way?

Pulling up to Blair's apartment, Dan unbuckles his seatbelt.

"My driver will take you home." Blair says, staring at his unbuckled seatbelt, quizzically.

"I'll help you up with your bags." Dan offers.

"That's not necessary." She says, a little curtly.

Dan ignores her and gets out of the car anyways. Before she can protest, he takes her bags out of the trunk and tells the driver not to wait. He figures he can just take a cab home. But Blair quickly tells the driver to disregard that and to please wait, Dan will be back down for his ride home soon.

"What are you doing?" She asks as they load the bags into the elevator.

"Carrying up your bags," Dan states again, matter-of-factly.

Blair glares at him, "You know what I mean. Why couldn't he have waited for you? If you're just helping me up to my apartment, it shouldn't take more than three minutes."

"How very precise," Dan echoes her terse tone.

They step off the elevator and march towards Blair's door, both frustrated with each other. Once the door is unlocked, Blair attempts to block him from entering by offering her hands. "I'll take it from here."

Dan refuses to hand over the bags and practically pushes past her to get in. Blair lets out a frustrated breath and follows him in. She slams the door as she asks, "What the fuck, Dan?"

Dan sets down the bags and then turns to face her. "So we just aren't going to talk about it? What? Are we just going to pretend it never happened?"

"What happened? I don't know what you're talking about." Blair sounds annoyed.

"Yes you do," Dan contradicts. "You know exactly what I'm talking about. We finally get our shit together and kiss after what? Two years? And now, that's that. We just go back to being just friends?"

Blair's eyes dart away as soon as he says the word kiss and the tension escalates. Finally, she meets his eye again and speaks in an unguarded voice. "I don't know."

"Well, I know what I want and it's not that. I want more, Blair. I want you." Dan says sincerely. The distance between them feels infinite as he stands across the room from her. He thinks of crossing the room toward her but knows he can't. He's already put himself on the line for her, it's her turn to make a move.

Blair shakes her head. "It won't work." She says in a fierce voice.

"Why won't it work?" Dan asks her, feeling confused.

"It's what I said from the beginning. There are only two possible outcomes. Scenario A and scenario B." She ticks each off her fingers.

Suddenly, it clicks for Dan. She was right all along. How hadn't he seen it? It was what she said when they first discussed the idea of pursuing something more and now she was reminding him.

"Scenario B. You regret it. Kissing me made you realize you don't want something more with me and now you can't even be friends with me." Dan looks at the ground, feeling deflated.

"No!" Blair says quickly, surprising Dan.

He looks back up at her, questioningly. "Then what do you mean?"

There's a pause before Blair says. "I just meant, that you know, it wouldn't work because _eventually_ one of those scenarios would happen. Not that they had."

Dan can tell she's trying to cover. After being her best friend for these past few years, he knows exactly when she's lying. He weighs how to respond. He thinks back to the wedding, how when he spoke unguardedly to her, she had finally been honest with him. He takes a deep breath before he speaks again.

"Scenario A." He says firmly and then pauses. "I should have just told you last night, in the garden. I don't know why I didn't, I guess I didn't want it to be too much too soon. But now I know, I should have told you right away how I felt, _how I feel_. I'm in love with you, Blair. And maybe if you reached the same conclusion that I did, then it won't end in disaster as you predicted."

Dan is filled with trepidation as he anxiously awaits her response. He tries to scan her face but her expression is unreadable as the silence grows.

"I didn't know. I thought…" She hesitates. "I thought you didn't. Because if you loved me too, then you would have agreed that we had wasted time not being together before. But you didn't seem to feel that way. You even said you would have fallen in love with me had you kissed me two years ago. Past tense."

Dan lets out a breath, "It didn't mean I hadn't fallen in love with you. Of course, I did, I was in love with you even before that night."

Blair doesn't say anything so Dan continues. "Just now, you said 'loved me too.'" Dan points out, a bubble of hope forming.

"No, I didn't." Blair interjects, quickly.

"You did. You definitely said 'too.'" Dan watches as she turns back to look at the door. He crosses the room to get to her before she can escape him and this conversation. He slowly takes her hands which he feels are trembling. "Blair?" He asks, willing her to look at him. Once she does, he says it again, steadily. "I'm in love with you and I want to be with you."

He sees now that he's up close how full of fear she his. Her eyes are wide with doubt and her hands still shake. Finally she speaks, "But what if it doesn't work? I need you, Dan. You're my best friend and I can't lose you."

"You won't lose me." Dan squeezes her hands, slightly.

"But it never works, look how many failed relationships we both have had."

"Because we weren't with the right person. I was always supposed to be with you." Dan snakes his arms around her waist, wanting to be closer to her.

"You're certain?" Blair still doesn't sound convinced.

"Of course, I'm certain. Now, can you be certain with me? Because I think three years is already too much time spent waiting." Dan says, leaning in toward her.

She nods and she meets her lips to his. After a few moments, she breaks away, "Three years? I thought it was two."

"I told you, I loved you long before that wedding." Dan starts to lean in again but she doesn't.

"There is _no_ way. You looked like you couldn't get away fast enough from that museum three years ago." Blair gives him a look.

"But that was before." Dan thinks about it. "Maybe more like 2 years and 10 months ago, if you want to be precise."

"That sounds more accurate." Blair gives a small laugh. "I know I fell in love with you when you let me steal your frozen hot chocolate at Serendipity."

"The only reason I ever let you swap was because I loved you." Dan tells her.

"Remember that one time Serena tried to trade frozen hot chocolates with you?" Blair says with a wry smile.

"I slapped her hand away. Only you're allowed." Dan says seriously.

"Good." Blair leans in and starts kissing him again.

But then Dan breaks the kiss, remembering in panic, "Your driver is still waiting for me downstairs, isn't he?"

Blair winces, "Shit, I forgot I told him to wait for you."

Dan glances at his bags, still on the ground near the door. "I should probably get back anyway, I have to go in to work in the morning."

Blair grasps his arms more fiercely. "No, you can't leave. I'll just call down and tell him you changed your mind. We won't be needing him until morning, he can drive you to work."

"But I'll still need my bags taken home. I can't bring them to work."

"You can just leave them here." Blair says, suggestively.

"So I'd have to come back here after work," Dan says with a smirk. "Clever."

"And every day after that. We have a lot of time to make up for." Blair points out.

Dan puts a finger to his chin, in mock contemplation. "True. Sounds like I better stay for awhile."

"Not just a while, permanently." Blair corrects him.

"Permanently" Dan echoes. "So want to give me a tour of my new permanent residence?"

Blair nods, dutifully. "Where would you like to tour first?"

"The bedroom?" Dan suggests.

"Right this way," Blair tugs him by the arm and puts on a mock tour guide voice. "Our first stop is the master bedroom complete with hardwood floors, french doors, crown modeling, and of course, a king-sized bed, as you can see..." Blair's faux tour fades away as she pulls Dan onto the bed and kisses him.

"Convinced yet?" She pulls away slightly to ask.

Dan nods, "I didn't really need any convincing." Then he presses his mouth back to hers.

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 **End :)**

 **I hope you all enjoyed this story! Since I knew this would be the final chapter, I really wanted to make sure I took my time writing it. So that's why it was so delayed. I am still continuing to write more Dair stories :) If you haven't seen, I started a new story called A Bittersweet Retreat which follows Blair and Dan into the** **wilderness.  
**

 **Also, question for you guys, should I try a Serenate story next? Maybe follow Nate and Serena to Portugal and Spain? Let me know your thoughts!**

 **Thank you so much for reading til the end of this one! And for leaving reviews, each and everyone is very appreciated so thanks again!**


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